3-Amino-2-methylbenzoic acid synthesis
- Product Name:3-Amino-2-methylbenzoic acid
- CAS Number:52130-17-3
- Molecular formula:C8H9NO2
- Molecular Weight:151.16
1975-50-4
52130-17-3
The general procedure for the synthesis of 3-amino-2-methylbenzoic acid from 2-methyl-3-nitrobenzoic acid was as follows: 2-methyl-3-nitrobenzoic acid (2 g, 12.12 mmol) was dissolved in ethyl acetate in a two-necked round-bottomed flask and 5% Pd-C catalyst (0.10 g) was added. The reaction mixture was stirred for 15 h under hydrogen atmosphere. After completion of the reaction, the solvent was removed by distillation under reduced pressure to give the crude product. The crude product was purified by column chromatography (silica gel 60-120 mesh, with dichloromethane and ethanol (v/v, 99.5:0.5) as eluents) to give a white solid product with a melting point of 181°C. IR (νmax, cm-1): 3244 (νN-H), 1724 (νC=O, acid), 1284 (νC-N, aromatic amine). Elemental analysis (C8H9NO2) Calculated values: C, 63.56%; H, 6.00%; N, 9.27%. Measured values: C, 63.13%; H, 5.87%; N, 8.99%.
1975-50-4
467 suppliers
$18.00/25g
52130-17-3
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$20.00/25g
Yield:52130-17-3 90%
Reaction Conditions:
with palladium on activated charcoal;hydrogen in ethyl acetate for 15 h;
Steps:
4 3-Amino-2-methyl-benzoic acid
2-Methyl-3-nitrobenzoic acid (2 g, 12.12 mmol) was dissolved in ethyl acetate in a two neck round bottom flask to it 5% Pd-C (0.10 g).
The reaction mixture is stirred for 15 h under balloon pressure filled with hydrogen gas.
On completion of the reaction the crude product was collected by evaporating the solvent under reduced pressure.
The crude product was then purified by column chromatography (silica gel 60-120 mesh, using dichloromethane and ethanol, (v/v, 99.5:0.5) as eluent to give pure white solid. mp: 181 °C. Yield: 1.5 g (90%). IR νmax in cm-1: 3244 (νN-H), 1724 (νC=O, acid), 1284 (νC-N, aromatic amine).
Elemental analysis calculated for C8H9NO2: C, 63.56%; H, 6.00%; N, 9.27%.; Found: C, 63.13%; H, 5.87%; N, 8.99%.
References:
Paul, Manoj Kumar;Kalita, Gayatri;Laskar, Atiqur Rahman;Debnath, Somen;Gude, Venkatesh;Sarkar, Dipika Debnath;Mohiuddin, Golam;Varshney, Sanjay Kumar;Nandiraju Rao [Journal of Molecular Structure,2013,vol. 1049,p. 78 - 89]
18583-89-6
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52130-17-3
340 suppliers
$20.00/25g