methyl 2-amino-4-chloro-5-methoxybenzoate

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 2-amino-4chloro-5-methoxybenzoic acid (3.0 g, 15.0 mmol; prepared according to the procedure of Denny, et al., J. Med. Chem. 34:217-222 (1991)) in 70 ml MeOH was treated with excess trimethylsilyl diazomethane. The solution was concentrated and the residue flash chromatographed on silica (9:1 hexane/EtOAc to give the title compound (46%): mp 63°-64° C.; 1H NMR (300 MHz, CDCl3) δ 6 3.83 (s, 3H), 3.90 (s, 3H), 5.48 (bs, 2H), 6.75 (s, 1H), 7.39 (s, 1H); MS (DCI/NH3) m/z 216 (M+H)+. prepared The solution was concentrated the residue flash chromatographed on silica (9:1 hexane/EtOAc

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 2-amino-4chloro-5-methoxybenzoic acid (3.0 g, 15.0 mmol; prepared according to the procedure of Denny, et al., J. Med. Chem. 34:217-222 (1991)) in 70 ml MeOH was treated with excess trimethylsilyl diazomethane. The solution was concentrated and the residue flash chromatographed on silica (9:1 hexane/EtOAc to give the title compound (46%): mp 63°-64° C.; 1H NMR (300 MHz, CDCl3) δ 6 3.83 (s, 3H), 3.90 (s, 3H), 5.48 (bs, 2H), 6.75 (s, 1H), 7.39 (s, 1H); MS (DCI/NH3) m/z 216 (M+H)+. prepared The solution was concentrated the residue flash chromatographed on silica (9:1 hexane/EtOAc