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Simple one-pot green method for large-scale production of mesalamine, an anti-inflammatory agent

  • C. Vijaya Lakshmi , Naresh Kumar Katari EMAIL logo and Sreekantha B. Jonnalagadda EMAIL logo
Published/Copyright: October 2, 2018
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Green Processing and Synthesis
From the journal Green Processing and Synthesis Volume 8 Issue 1

Abstract

We report a rapid and efficient synthesis protocol for mesalamine via a green approach with 2-chloro-5-nitrobenzoic acid as the starting material, for its large-scale production. This one-pot method involves the conversion of a chloro group into a hydroxyl group using aqueous KOH solution, followed by the reduction of a nitro group to amine using Pd/C. The product was characterised and confirmed by 1H-nuclear magnetic resonance (NMR), 13C NMR, IR and mass spectrometry techniques. The salient features of the method include excellent conversion (99.3%), high yield (93%), cost effectiveness and validated results for benign, large-scale production.

Keywords: anti-inflammatory; green approach; mesalamine; one pot synthesis; Pd/C

1 Introduction

Inflammation is a protecting mechanism utilised by tissues against endogenous and exogenous antigens, induced by microbial infection or tissue injury and is characterised by redness, enema, fever, pain, and loss of performance. Inflammation associated with various chronic diseases including arterial sclerosis, obesity, diabetes, neurodegenerative diseases and even cancer, is a serious health concern [1], [2]. Non-steroidal medication (NSAIDs) is widely used for the treatment of inflammatory and painful conditions, as well as autoimmune disease, soft tissue lesions, fever and urinary tract infections [3], [4]. The activity of NSAIDs results from protein inhibition of cyclooxygenase (COX) mediated production of pro-inflammatory prostaglandins and thromboxanes [5]. COX enzymes exist in three isoforms: COX-1, COX-2 and COX-3 [6], [7]. COX-1 is the constitutional enzyme in most cells and plays an important role in the protection of the stomach tissue layer, protoplasm aggregation and nephritic blood flow. The COX (COX-1 and COX–2) is associated with nursing inducible isozyme system, and is considerably expressed throughout inflammation, pain, and oncogenesis [7], whereas COX-3, a splice variant of COX-1, is taken into account as another target for drugs [6], [7], [8]. Conventional NSAIDs inhibit COX-1 and COX-2 and therefore their administration usually causes epithelial duct [9], [10], renal [11], [12], and hepatic effects [13].

Mesalamine belongs to the class of salicylates, which are known to exhibit anti-inflammatory activity. It is also a key intermediate for sulphasalazine, olsalazine and balsalazide [14]. It is slightly soluble in dehydrated alcohol and methyl alcohol and insoluble in chloroform, ether, n-hexane and ester. It is prescribed for the treatment and management of colitis. It primarily provides relief from pain to some extent in patients affected by this disease [15], [16], [17], [18], [19], [20], [21]. 5-Aminosalicylic acid is an active medicine for colitis due to its multiple actions on numerous functions of the immune system [22], [23].

Mesalamine is a simple compound, but is difficult to prepare in high purity and in good yields, especially on a large scale. Few synthetic routes for mesalamine are reported in the literature, such as the coupling of diazonium salt derived from sulfanilic acid with salicylic acid [24]. In this method, the product undergoes hydrogenation, resulting in low purity and yield. Another method based on the condensation of phenyl diazonium salt with salicylic acid, followed by hydrogenation to give the desired mesalamine, is also reported [25]. A protocol involving the nitration of salicylic acid followed by reduction to form the target compound is also described, but with low purity and yield [26]. A two-step procedure involving carboxylation of p-acetaminophenol or p-aminophenol in the presence of a solid base catalyst is reported to give a 63% yield [27]. Generally, upscaling the laboratory experiments and their large-scale production is challenging [28], [29].

Motivated by the application of mesalamine in inflammation control, we attempted the one-pot synthesis of mesalamine from 2-chloro-5-nitrobenzoic acid, to broaden its scope for industrial scale production. In this communication, we describe an efficient one-pot method in which 2-chloro-5-nitrobenzoic acid is converted to 2-hydroxy-5-nitrobenzoic acid using excess aqueous KOH (4.0 equivalents) to ensure completion of hydrolysis; this is further converted to the desired product, mesalamine, under hydrogen atmosphere using 10% Pd/C as the catalyst. By this strategy, the target compound, mesalamine, was obtained in an excellent yield (93%). Tables 1 and 2 summarise the results of the optimisation of the reaction conditions.

Table 1:

Optimisation of reaction conditions for the preparation of 2-hydroxy-5-nitrobenzoic acid (2).

Sample no.BaseEquivalentsTime (h)Temperature (°C)Conversion (%)
1Aq. Na2CO34.024110No conversion
2Aq. Na2CO34.024130No conversion
3Aq. NaOH4.0611057.6
4Aq. NaOH4.0811071.0
5Aq. NaOH4.02411071.9
6Aq. NaOH4.0613059.8
7Aq. NaOH4.0813063.5
8Aq. NaOH4.01213074.5
9Aq. NaOH4.02413079.6
10Aq. KOH4.0611072.5
11Aq. KOH4.0811077.0
12Aq. KOH4.01211082.5
13Aq. KOH4.02411088.0
14Aq. KOH4.0613092.9
15Aq. KOH4.0813098.9

  1. Bold face values are best optimization conditions.

Table 2:

Optimisation of reaction conditions for the preparation of 2-hydroxy-5-amino benzoic acid (1).

Sample no.Time (h)Temperature (°C)Catalyst (% Pd/C)Conversion (%)
12605No
2860526
31660555
42601068.2
52801069.0
64601075.2
74801077
86601082.0
96801082.5
107601093.0
11880529.0
128601099.3

  1. Bold face values are best optimization conditions.

2 Materials and methods

2.1 General methods

AR grade reagents and solvents were used without further purification. All the reactions were carried out in oven-dried flasks. IR spectra were recorded on a Perkin-Elmer 1000 instrument (Sigma-Aldrich, Delhi, India) in the KBr phase and absorptions are reported in cm−1. Nuclear magnetic resonance (NMR) spectra were recorded on 400 MHz (Varian) spectrometers in appropriate solvents using tetramethylsilane as the internal standard, or the solvent signals as secondary standards, and the chemical shifts are shown in δ scales. Multiplicities of NMR signals are designated as s (singlet), d (doublet), t (triplet), q (quartet), br (broad), m (multiplet for unresolved lines), etc. Mass spectra were recorded with a PE Scitex model API 3000 instrument. The compound was also analysed by high performance liquid chromatography (HPLC) for purity.

2.2 Large-scale preparation of mesalamine

Based on the success of the laboratory synthesis of the target compound in excellent yields and high purity, we successfully scaled up the quantities of reactants for large-scale production. 2-Chloro-5-nitrobenzoic acid (1 kg) was added to a stirred solution of KOH (1.4 kg) in water (6 l) over a period of 40 min at 30–35°C in an autoclave. The resulting mixture was stirred at 130°C for 7–8 h in a closed autoclave under 2.5–3 kg/cm2 pressure. Then, the reaction mixture was cooled to 30°C and charged with 10% wet Pd/C (60 g) at 30–35°C under nitrogen atmosphere. After the removal of nitrogen gas, the resulting mixture in the autoclave was purged with hydrogen gas at 6–8 kg/cm2 pressure and heated at 60–65°C for 8 h. After completion of reduction, the mixture was cooled to 30–35°C and the catalyst was filtered through celite and washed with water (500 ml). The aqueous layer was treated with sodium hydrosulphite (20 g), in ethyl acetate (1 l) at 30–35°C for 30 min. The pH of the solution was adjusted to 3.5–4.5 by adding concentrated hydrochloric acid and then stirred for 1 h. The solid was filtered and washed with water (1 l). The resulting solid was added to water (6 l) and the pH adjusted to 0.6–0.9 with 10% HCl solution and continuously stirred for about 30 min, until it resulted in a clear solution. The mixture was heated to 45–50°C and treated with sodium hydrosulphite (20 g) and active charcoal (30 g) at the same temperature for 30 min. The resultant solution was filtered through celite, washed with water (50 ml) and then mixed with ethyl acetate (50 ml) to obtain the filtrate. The pH of the solution was adjusted to 3.5–4.0 with aqueous sodium carbonate (10%) solution followed by stirring for 1 h at 30–35°C and then filtered. The resulting solid was washed with water (500 ml) followed by acetone (500 ml), dried at 65–70°C for 8–9 h to give the off-white solid (3). The yield was 93% with 99.95% purity. The filtered wet Pd/C catalyst material was transferred into a closed beaker under nitrogen atmosphere. For safety precautions, Pd/C was always kept submerged under water after recovery and ready for reuse.

IR: 3445, 2979, 1796, 1314 cm−1; 1H NMR (400 MHz, DMSO) δ=6.65 (d, 1H, J=8.1 Hz), 6.84 (dd, 1H, J=8.2, 2.3 Hz), 7.18 (d, 1H, J=2.3 Hz), 8.64 (brs, 2H); LCMS: m/z 154 (M+H)+; 13C NMR (100 MHz, DMSO): δ=114.7, 116.9, 117.1, 123.9, 134.7, 155.3, 177.7; HPLC: 99.95% pure.

3 Results and discussion

In the preliminary experiments, we investigated the conversion of 2-chloro-5-nitrobenzoicacid (1) to 2-hydroxy-5-nitrobenoicacid (2) in various alkaline conditions, using sodium carbonate, NaOH or KOH under various reaction parameters such as time and temperature. Progress of the reaction was monitored by analysing for formation of the intermediate employing HPLC and the results are tabulated in Table 1. Use of sodium carbonate resulted in incomplete conversion and NaOH gave 79.6% conversion, while KOH facilitated 98.9% conversion.

The conversion efficacy of 2-hydroxy-5-nitrobenzoic acid (2) to mesalamine (3) under varied conditions was examined. The use of 5% Pd/C as a catalyst under hydrogen atmosphere at 60°C reaction resulted in a 40% yield. The use of 10% Pd/C under similar conditions gave an excellent yield (93%) of mesalamine. Table 2 summarises the results, reflecting the effect of various controlling parameters, the catalyst loading, reaction time, and temperature on the yield of the desired product.

NMR, IR, HPLC and mass spectra of the synthesized compounds are reported in Supplementary Information available.

4 Conclusion

In summary, we developed a rapid and efficient one-pot method for the large-scale production of mesalamine via a green approach with 2-chloro-5-nitrobenzoic acid as the starting material. The proposed method, which gives an excellent yield of the desired product with minimal side reactions, proves superior to existing protocols for the production of the valuable drug, 2-hydroxy-5-amino benzoic acid, and offers an opportunity for safe industrial production.

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Supplementary Material

The online version of this article offers supplementary material (https://doi.org/10.1515/gps-2018-0108).

Received: 2018-06-04
Accepted: 2018-08-10
Published Online: 2018-10-02
Published in Print: 2019-01-28

©2019 Walter de Gruyter GmbH, Berlin/Boston

This work is licensed under the Creative Commons Attribution 4.0 Public License.

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https://doi.org/10.1515/gps-2018-0108
Keywords for this article
anti-inflammatory; green approach; mesalamine; one pot synthesis; Pd/C
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  29. Mechano-chemical synthesis of ammonia and acetic acid from inorganic materials in water
  30. Green synthesis and structural characterization of novel N1-substituted 3,4-dihydropyrimidin-2(1H)-ones
  31. Biodiesel production from cotton oil using heterogeneous CaO catalysts from eggshells prepared at different calcination temperatures
  32. Regeneration of spent mercury catalyst for the treatment of dye wastewater by the microwave and ultrasonic spray-assisted method
  33. Green synthesis of the innovative super paramagnetic nanoparticles from the leaves extract of Fraxinus chinensis Roxb and their application for the decolourisation of toxic dyes
  34. Biogenic ZnO nanoparticles: a study of blueshift of optical band gap and photocatalytic degradation of reactive yellow 186 dye under direct sunlight
  35. Leached compounds from the extracts of pomegranate peel, green coconut shell, and karuvelam wood for the removal of hexavalent chromium
  36. Enhancement of molecular weight reduction of natural rubber in triphasic CO2/toluene/H2O systems with hydrogen peroxide for preparation of biobased polyurethanes
  37. An efficient green synthesis of novel 1H-imidazo[1,2-a]imidazole-3-amine and imidazo[2,1-c][1,2,4]triazole-5-amine derivatives via Strecker reaction under controlled microwave heating
  38. Evaluation of three different green fabrication methods for the synthesis of crystalline ZnO nanoparticles using Pelargonium zonale leaf extract
  39. A highly efficient and multifunctional biomass supporting Ag, Ni, and Cu nanoparticles through wetness impregnation for environmental remediation
  40. Simple one-pot green method for large-scale production of mesalamine, an anti-inflammatory agent
  41. Relationships between step and cumulative PMI and E-factors: implications on estimating material efficiency with respect to charting synthesis optimization strategies
  42. A comparative sorption study of Cr3+ and Cr6+ using mango peels: kinetic, equilibrium and thermodynamic
  43. Effects of acid hydrolysis waste liquid recycle on preparation of microcrystalline cellulose
  44. Use of deep eutectic solvents as catalyst: A mini-review
  45. Microwave-assisted synthesis of pyrrolidinone derivatives using 1,1’-butylenebis(3-sulfo-3H-imidazol-1-ium) chloride in ethylene glycol
  46. Green and eco-friendly synthesis of Co3O4 and Ag-Co3O4: Characterization and photo-catalytic activity
  47. Adsorption optimized of the coal-based material and application for cyanide wastewater treatment
  48. Aloe vera leaf extract mediated green synthesis of selenium nanoparticles and assessment of their In vitro antimicrobial activity against spoilage fungi and pathogenic bacteria strains
  49. Waste phenolic resin derived activated carbon by microwave-assisted KOH activation and application to dye wastewater treatment
  50. Direct ethanol production from cellulose by consortium of Trichoderma reesei and Candida molischiana
  51. Agricultural waste biomass-assisted nanostructures: Synthesis and application
  52. Biodiesel production from rubber seed oil using calcium oxide derived from eggshell as catalyst – optimization and modeling studies
  53. Study of fabrication of fully aqueous solution processed SnS quantum dot-sensitized solar cell
  54. Assessment of aqueous extract of Gypsophila aretioides for inhibitory effects on calcium carbonate formation
  55. An environmentally friendly acylation reaction of 2-methylnaphthalene in solvent-free condition in a micro-channel reactor
  56. Aegle marmelos phytochemical stabilized synthesis and characterization of ZnO nanoparticles and their role against agriculture and food pathogen
  57. A reactive coupling process for co-production of solketal and biodiesel
  58. Optimization of the asymmetric synthesis of (S)-1-phenylethanol using Ispir bean as whole-cell biocatalyst
  59. Synthesis of pyrazolopyridine and pyrazoloquinoline derivatives by one-pot, three-component reactions of arylglyoxals, 3-methyl-1-aryl-1H-pyrazol-5-amines and cyclic 1,3-dicarbonyl compounds in the presence of tetrapropylammonium bromide
  60. Preconcentration of morphine in urine sample using a green and solvent-free microextraction method
  61. Extraction of glycyrrhizic acid by aqueous two-phase system formed by PEG and two environmentally friendly organic acid salts - sodium citrate and sodium tartrate
  62. Green synthesis of copper oxide nanoparticles using Juglans regia leaf extract and assessment of their physico-chemical and biological properties
  63. Deep eutectic solvents (DESs) as powerful and recyclable catalysts and solvents for the synthesis of 3,4-dihydropyrimidin-2(1H)-ones/thiones
  64. Biosynthesis, characterization and anti-microbial activity of silver nanoparticle based gel hand wash
  65. Efficient and selective microwave-assisted O-methylation of phenolic compounds using tetramethylammonium hydroxide (TMAH)
  66. Anticoagulant, thrombolytic and antibacterial activities of Euphorbia acruensis latex-mediated bioengineered silver nanoparticles
  67. Volcanic ash as reusable catalyst in the green synthesis of 3H-1,5-benzodiazepines
  68. Green synthesis, anionic polymerization of 1,4-bis(methacryloyl)piperazine using Algerian clay as catalyst
  69. Selenium supplementation during fermentation with sugar beet molasses and Saccharomyces cerevisiae to increase bioethanol production
  70. Biosynthetic potential assessment of four food pathogenic bacteria in hydrothermally silver nanoparticles fabrication
  71. Investigating the effectiveness of classical and eco-friendly approaches for synthesis of dialdehydes from organic dihalides
  72. Pyrolysis of palm oil using zeolite catalyst and characterization of the boil-oil
  73. Azadirachta indica leaves extract assisted green synthesis of Ag-TiO2 for degradation of Methylene blue and Rhodamine B dyes in aqueous medium
  74. Synthesis of vitamin E succinate catalyzed by nano-SiO2 immobilized DMAP derivative in mixed solvent system
  75. Extraction of phytosterols from melon (Cucumis melo) seeds by supercritical CO2 as a clean technology
  76. Production of uronic acids by hydrothermolysis of pectin as a model substance for plant biomass waste
  77. Biofabrication of highly pure copper oxide nanoparticles using wheat seed extract and their catalytic activity: A mechanistic approach
  78. Intelligent modeling and optimization of emulsion aggregation method for producing green printing ink
  79. Improved removal of methylene blue on modified hierarchical zeolite Y: Achieved by a “destructive-constructive” method
  80. Two different facile and efficient approaches for the synthesis of various N-arylacetamides via N-acetylation of arylamines and straightforward one-pot reductive acetylation of nitroarenes promoted by recyclable CuFe2O4 nanoparticles in water
  81. Optimization of acid catalyzed esterification and mixed metal oxide catalyzed transesterification for biodiesel production from Moringa oleifera oil
  82. Kinetics and the fluidity of the stearic acid esters with different carbon backbones
  83. Aiming for a standardized protocol for preparing a process green synthesis report and for ranking multiple synthesis plans to a common target product
  84. Microstructure and luminescence of VO2 (B) nanoparticle synthesis by hydrothermal method
  85. Optimization of uranium removal from uranium plant wastewater by response surface methodology (RSM)
  86. Microwave drying of nickel-containing residue: dielectric properties, kinetics, and energy aspects
  87. Simple and convenient two step synthesis of 5-bromo-2,3-dimethoxy-6-methyl-1,4-benzoquinone
  88. Biodiesel production from waste cooking oil
  89. The effect of activation temperature on structure and properties of blue coke-based activated carbon by CO2 activation
  90. Optimization of reaction parameters for the green synthesis of zero valent iron nanoparticles using pine tree needles
  91. Microwave-assisted protocol for squalene isolation and conversion from oil-deodoriser distillates
  92. Denitrification performance of rare earth tailings-based catalysts
  93. Facile synthesis of silver nanoparticles using Averrhoa bilimbi L and Plum extracts and investigation on the synergistic bioactivity using in vitro models
  94. Green production of AgNPs and their phytostimulatory impact
  95. Photocatalytic activity of Ag/Ni bi-metallic nanoparticles on textile dye removal
  96. Topical Issue: Green Process Engineering / Guest Editors: Martine Poux, Patrick Cognet
  97. Modelling and optimisation of oxidative desulphurisation of tyre-derived oil via central composite design approach
  98. CO2 sequestration by carbonation of olivine: a new process for optimal separation of the solids produced
  99. Organic carbonates synthesis improved by pervaporation for CO2 utilisation
  100. Production of starch nanoparticles through solvent-antisolvent precipitation in a spinning disc reactor
  101. A kinetic study of Zn halide/TBAB-catalysed fixation of CO2 with styrene oxide in propylene carbonate
  102. Topical on Green Process Engineering
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