Formamide → 4-AMINO-3-CHLOROBENZAMIDE

Participants

Reaction Steps

An anhydrous DMF solution of 1.00 g (5.39 mmol) of methyl 4-amino-3-chlorobenzoate (17-1), 728 mg (16.16 mmol) of formamide and 204 mg (3.77 mmol) of 5.5M sodium methoxide was stirred for 1 hour at 100° C. and then stirred overnight at room temperature. The reaction was poured into 2-propanol (60 mL) and then evaporated off the solvent. The resultant crude oil was purified on a silica column and eluted with DCM:MeOH:NH4OH (95:5:0.5 to 9:1:0.1). Recovered the desired product 17-2. MS (M+1): measured 171.2; theoretical 170.0. 1H NMR (DMSO): 5.86 (s, 2H), 6.75 (d, 1H), 7.01 (bs, 1H), 7.56 (dd, 1H), 7.66 (bs, 1H), 7.75 (m, 1H).

Provenance & Evidence