4-Chloroaniline → HCID 23141392, compound

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Reaction Conditions

Reaction Steps

5-(Methoxycarbonyl)-2-nitrobenzoic acid (CAS registry number: 76143-33-4) (1.50 g) and 0.05 mL of N,N-dimethylformamide were dissolved in 150 mL of dichloromethane, and the solution was cooled to 0° C. To this solution, 0.87 mL of oxalyl chloride was added little by little, and the mixture was stirred for 30 minutes at 0° C., followed by stirring the mixture for 13 hours at room temperature. The reaction mixture was distilled under reduced pressure, and dried to obtain a light yellow solid, which was dissolved in 150 mL of dichloromethane. To this solution, a solution of 0.94 g of 4-chloroaniline and 3.57 mL of N,N-diisopropylethylamine dissolved in 25 mL of dichloromethane was added little by little. The mixture was stirred for 2 hours and a half at room temperature, whereafter 100 mL of a saturated aqueous solution of ammonium chloride was added to separate the organic layer. The aqueous layer was extracted twice with 50 mL of dichloromethane. The respective organic layers were combined, whereafter the combined organic layer was washed with 50 mL of a saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate. The anhydrous sodium sulfate was separated by filtration, and washed with dichloromethane. The filtrate and the washings were combined, and dichloromethane was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography. The resulting solid was dried under reduced pressure to obtain 1.82 g (81%) of methyl N-(4-chlorophenyl)-4-nitroisophthalamate.

Provenance & Evidence