Réaction #66053

Équation de réaction

3-aminobenzoic acid

MeOH

thionyl chloride

→

title compound

Rendement 98.0%

Methyl 3-amino-benzoate hydrochloride

Rendement 98.0%

Conditions de réaction

Traitement

1. 1
   Autrewas removed by evaporation
2. 2
   Autrethe product precipitated with diethyl ether
3. 3
   AutreThe diethyl ether was removed by evaporation

Mode opératoire

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