4-Chlorobenzylamine → HCID 178522950, compound

Participants

Reaction Steps

A solution of ethyl 4-hydroxy-6-iodo-3-cinnolinecarboxylate (0.27 g, 0.79 mmol) and 4-chlorobenzylamine (3.50 mL, 28.77 mmol) is heated at 90° C. for 30 minutes. The reaction is cooled slightly and poured into 25 mL EtOAc. Hexanes are added to precipitate the product and the resulting solid is filtered and dried. The product is further purified by trituration with CH2Cl2/hexanes (0.29 g, 0.67 nmmol, 85%). Physical characteristics are as follows: m.p. 307-308° C.; 1H NMR (300 MHz, DMSO-d6) δ 9.99, 8.47, 8.15, 7.57, 7.40, 4.55; IR (drift) 2972, 2958, 2901, 2846, 1645, 1601, 1557, 1488, 1458, 1356, 933, 922, 822, 806, 722 cm−1; MS (ESI) m/z 439.8 (M+H)+, 437.8 (M—H)−; Anal. Calcd for C16H11ClIN3O2: C, 43.71; H, 2.52; N, 9.56; Found: C, 43.94; H, 2.50; N, 9.43.

Provenance & Evidence