4-Chloroaniline → HCID 11624546, compound

Participants

Reaction Conditions

Reaction Steps

4-Chloroaniline (957 mg, 7.5 mmol) was dissolved in pyridine (25 mL). The resulting mixture was cooled down to 0° C. Methyl 3-(4-chlorosulphonyl)phenylpropionate (1.314 g, 5.0 mmol) was added in portions. The mixture was stirred between 0° C. and room temperature overnight. Solvents were evaporated to dryness. The crude oil was dissolved in ethyl acetate (30 mL) and washed with 10% HCl (2×15 mL) and brine (1×15 mL). Organic phase was dried over magnesium sulfate before filtering and removal of solvent. The desired product, e.g. methyl 3-{4-[(4-chloroanilino)sulfonyl]phenyl}propanoate (1.458 g, 82.4%), was obtained as a colorless solid, in 98.5% purity by HPLC (MaxPlot detection between 230 and 400 nm).

Provenance & Evidence