Methanol → HCID 18771474, compound

Participants

Reaction Steps

To a suspension of 4-(aminomethyl)benzoic acid (10 g, 66 mmol) in MeOH (100 mL) at 0° C. was added SOCl2 (5.3 mL, 73 mmol) dropwise. The ice bath was removed and the reaction stirred at rt overnight. After heating the reaction at reflux for 4 h, the solvent was evaporated. The residue was suspended in CH2Cl2 (100 mL) at 0° C. and triethylamine (25 mL) was added, followed by the dropwise addition of methanesulfonyl chloride (7.75 mL, 100 mmol). The reaction was stirred at rt for 1 h, poured into ice H2O, extracted with CH2Cl2, dried over anhydrous Na2SO4, filtered and evaporated. The crude product was flash chromatographed on silica gel eluting with 1% MeOH/CHCl3. The title compound was isolated as a white solid (11.8 g, 74%): 1H NMR (CDCl3): d 8.03 (d, 2H); 7.42 (d, 2H); 4.9 (br t, 1H); 4.38 (d, 2H); 3.92 (s, 3H); 2.89 (s, 3H).

Provenance & Evidence