3-Amino-2-methylbenzoic acid synthesis

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 ν_max in cm^-1: 3244 (ν_N-H), 1724 (ν_C=O, acid), 1284 (ν_C-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]

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