Reaction #66053

Reaction equation

3-aminobenzoic acid

MeOH

thionyl chloride

→

title compound

Yield 98.0%

Methyl 3-amino-benzoate hydrochloride

Yield 98.0%

Conditions

Workup

1. 1
   Otherwas removed by evaporation
2. 2
   Otherthe product precipitated with diethyl ether
3. 3
   OtherThe diethyl ether was removed by evaporation

Procedure

To a suspension of 3-aminobenzoic acid (1.03 g mg, 7.52 mmol) in MeOH (80 mL) at 0° C. was added dropwise thionyl chloride (5 mL). The resulting solution was allowed to stir for 16 h before the solvent was removed by evaporation and the product precipitated with diethyl ether. The diethyl ether was removed by evaporation to yield the title compound (1.38 g, 7.38 mmol, 98%) as a white solid. Mp 176-178° C. 1H NMR (D2O, 300 MHz): δ 7.75 (dt, J=1.8, 3.3, 7.2 Hz, 1H, ArH); 7.71 (m, 1H, ArH); 7.42 (m, 1H, ArH); 7.37 (m, 1H, ArH); 3.66 (s, 31H, OCH3). Mass Spectrum (C1) m/z 152 (100%) [M+]. HRMS calcd for C8H10NO2 152.0712, found 152.0698.

Source