反応 #66053

反応方程式

3-aminobenzoic acid

MeOH

thionyl chloride

→

title compound

収率 98.0%

Methyl 3-amino-benzoate hydrochloride

収率 98.0%

反応条件

後処理

1. 1
   その他was removed by evaporation
2. 2
   その他the product precipitated with diethyl ether
3. 3
   その他The diethyl ether was removed by evaporation

実験手順

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.

出典