4-Chloroaniline → HCID 11323731, compound

Participants

Reaction Steps

A solution of homophthalic anhydride (4.0 g, 24.7 mmol) in 250 mL of CHCl3 was treated with 4-chloroaniline (3.31 g, 25.9 mmol). After 16 h, the mixture was poured into EtOAc and 1 N NaOH. The aqueous layer was washed with EtOAc, then brought to a pH of 2-3 by addition of 1 N HCl. The aqueous layer was washed with EtOAc (2×), and the combined extracts were dried (MgSO4) and concentrated. Recrystallization of the residue from EtOAc/hexanes yielded 3.41g (48%) of the title compound.

Provenance & Evidence