Reaktion #66053

Reaktionsgleichung

3-aminobenzoic acid

MeOH

thionyl chloride

→

title compound

Ausbeute 98.0%

Methyl 3-amino-benzoate hydrochloride

Ausbeute 98.0%

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigewas removed by evaporation
2. 2
   Sonstigethe product precipitated with diethyl ether
3. 3
   SonstigeThe diethyl ether was removed by evaporation

Vorschrift

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.

Quelle