Pyridine → HCID 68426884, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 2-aminophenol (2.5 g, 22.9 mmol) in dry methylene chloride (10 mL) was added to a mixture of 4-bromo-3-chlorosulfonyl-5-methyl-benzoic acid methyl ester (7.18 g, 22.9 mmol) and dry pyridine (10 mL, 124.7 mmol) in methylene chloride (40 mL). The reaction mixture was stirred for 1 h at 10° C. and at room temperature overnight. It was concentrated, treated with 10% HCl (100 mL) and extracted with 1-butanol. The organic layer was washed with water, brine, dried, concentrated, treated with methanolic HCl (60 ml) and refluxed for 3 h. The reaction mixture was concentrated, treated with 10% aqueous sodium bicarbonate solution to alkaline pH and extracted using ethyl acetate. The organic layer was washed with water, brine, dried and purified, using flash chromatography (silica gel, 10% ethyl acetate/pet ether) to obtain the title compound. Yield: 2.2 g, (24%); 1H NMR (CDCl3): δ 2.4 (s, 3H, CH3), 3.9 (s, 3H, OCH3), 6.6 (t, 1H, Ar), 6.72 (t, 1H, Ar), 6.74 (d, 1H, Ar), 7.2 (d, 1H, Ar), 7.94 (s, 1H, OH), 7.96 (s, 1H, Ar), 8.5 (s, 1H, Ar); MS: m/e (EI+) 400 (M+1).

Provenance & Evidence