Hydrochloric Acid → Ethyl 6-chloro-4-(phenylamino)nicotinate

Participants

Reaction Steps

A solution of ethyl 4,6-dichloronicotinate (16 g, 73 mmol), aniline (8.2 g, 88 mmol) and cone. HCl (0.5 mL) in EtOH (100 mL) was heated at reflux overnight. The solvent was removed under reduced pressure. Water was added and the solution was basified to pH 8 and extracted with EtOAc. The combined extracts were washed with brine, dried (MgSO4), and concentrated in vacuo. The residue was purified by chromatography to give ethyl 6-chloro-4-(phenylamino)nicotinate (10 g, 50% yield). 1H NMR (40 MHz, DMSO-d6): δ 9.73 (s, 1 H), 8.67 (s, 1 H), 7.50-7.46 (m, 2 H), 7.36-7.31 (m, 3 H), 6.78 (s, 1 H), 4.37 (q, J=7.2 Hz, 2 H), 1.35 (t, J=7.2 Hz, 3 H).

Provenance & Evidence