Triethylamine → HCID 178515070, compound

Participants

Reaction Steps

To a stirred suspension of dimethyl7-chloro-4-hydroxyquinoiine-2,3-dicarboxylate (1.90 g, 6.40 mM) and 4-bromophenyi hydrazine hydrochloride (10.0 g, 44.7 mM) in ethanol (35mL) was added triethylamine (7.1 mL, 51.1 mM). The resulting brown solutionwas refluxed for 22 hours during which time a tan precipitate formed. This mixture was cooled to room temperature and filtered to give the 4-bromophenyl hydrazine salt of the title compound as a white powder (1.69g). This material was refluxed in glacial acetic acid (20 mL) for 3 hours and cooled to room temperature. The resulting tan suspension was filtered and the solids washed with glacial acetic acid and then ether to give the title compound (1.15 g, 43%) as a tan powder, mp 393°-394° C.; MS(CI): 420 (M+H).

Provenance & Evidence