4-Chloroaniline → HCID 23141453, compound

Participants

Reaction Conditions

Reaction Steps

1-Ethyl 4-methoxyisophthalate (100 mg) obtained in step D of Example 1-2-1, and 2 μL of N,N-dimethylformamide were dissolved in 5 mL of dichloromethane, and the solution was cooled to 0° C. To this solution, 59 μL of oxalyl chloride was added little by little, and the mixture was stirred for 20 minutes at 0° C., followed by stirring the mixture for 16 hours at room temperature. The reaction mixture was distilled under reduced pressure, and dried to obtain a light yellow solid. This solid was dissolved in 3 mL of dichloromethane, and the solution was added to a solution of 63 mg of 4-chloroaniline and 234 μL of N,N-diisopropylethylamine dissolved in 2 mL of dichloromethane. The mixture was stirred for 3 hours at room temperature, and then dichloromethane was distilled off under reduced pressure. The resulting residue was purified by column chromatography (5 g of silica gel) using a 1:1 mixture of dichloromethane and n-hexane as an elution solvent, thereby obtaining 134 mg (94%) of ethyl N-(4-chlorophenyl)-4-methoxyisophthalamate.

Provenance & Evidence