Methyl 4-chloroanthranilate → HCID 57576651, compound

Participants

Reaction Steps

Methyl 2-amino-4-chlorobenzoate (200 mg, 1.1 mmol) and diisopropylethylamine (285 μL, 1.6 mmol) were dissolved in a solution of dichloromethane (4 mL) and dimethylformamide (2 mL). 3-Chlorothiophene-2-carbonyl chloride (235 mg, 1.3 mmol) was added dropwise. The reaction mixture was stirred overnight at room temperature. The solvent was removed under vacuum and the residue was re-dissolved in 25 mL of ethyl acetate. The reaction mixture was washed one time each with 10 mL portions of water, 0.1 M NaOH, and saturated aqueous NaCl. The organic layer was dried with MgSO4 and 90 mg of solid was precipitated by the addition of hexanes. The material was used without further purification. MS (EI) for C13H9Cl2NO3S: 330 (M+H).

Provenance & Evidence