2,4-Difluoroaniline → HCID 58962861, compound

Participants

Reaction Steps

2,4-Difluoroaniline (1.20 g, 9.3 mmol) and ethyl 4,6-dichloronicotinate (2.05 g, 9.3 mmol) were dissolved in a mixture of EtOH (40 ml) and conc. HCl (5 drops) and heated to reflux for 15 h. The solution was allowed to cool and H2O (3 drops) was added to initialize precipitation. The flask was then sealed and placed in a freezer for 3 h. The solid was then isolated by filtration and washed with 10% Et2O/Hexane, affording ethyl 6-chloro-4-(2,4-difluoroanilino)nicotinate (1.87 g, 64%); m.p. (EtOH/water) 107-109° C. 1H NMR [400 MHz, CDCl3] δ 9.62 (br s, 1H), 8.79 (s, 1H), 7.35-7.29 (m, 1H), 7.02-6.95 (m, 2H), 6.58 (d, J=1.5 Hz, 1H), 4.42 (q, J=7.1 Hz, 2H), 1.43 (t, J=7.1 Hz, 3H). MS (FAB+) 313 (50%).

Provenance & Evidence