2-Amino-6-chlorobenzoic acid → HCID 68865411, compound

Participants

Reaction Steps

A solution of 6-chloroanthranilic acid (1.9549 g, 11.57 mmol) in 4:1 benzene/methanol (58 mL) was treated with trimethylsilyldiazomethane (7.0 mL, 14.0 mmol, 2.0M solution in hexanes), stirred for 18 hours, quenched with acetic acid (1 mL), and concentrated. The concentrate (2.04 g, 10.99 mmol) was dissolved in pyridine (22 mL), treated with 2-fluorobenzenesulfonyl chloride (1.75 mL, 13.19 mmol), stirred for 18 hours, quenched with 1N HCl (200 mL), and treated with ethyl acetate (100 mL). The organic layer was washed with brine (100 mL), dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash column chromatography (3:1 hexanes/ethyl acetate) to provide the desired product (2.50 g, 66%). MS (ESI(+)) m/e 361 (M+H)+, 366 (M+NH4)+; MS (ESI(−)) m/e 342 (M−H)−; 1H NMR (300 MHz, DMSO-d6) δ 10.52 (br s, 1H), 7.72 (m, 2H), 7.43 (m, 3H), 7.37 (td, 1H), 7.22 (dd, 1H), 3.68 (s, 3H).

Provenance & Evidence