Ethyl 4-(4-methoxybenzylamino)-6-chloropyridine-3-carboxylate → Ethyl 4-amino-6-chloronicotinate

Participants

Reaction Steps

Heat a mixture of ethyl 6-chloro-4-(4-methoxybenzylamino)nicotinate (21 g, 65.6 mmol) and TFA (150 mL) at 50° C. overnight. Cool the mixture to RT, concentrate to dryness, dissolve the residue in EtOAc, wash with satd. NaHCO3 (2×), then brine (1×), dry over MgSO4, concentrate and purify via silica gel chromatography to give the title compound (10 g, 76%). 1H NMR (400 MHz, DMSO-d6): δ 8.49 (s, 1H), 7.47 (s, 2H), 6.76 (s, 1H), 4.29 (q, J=7.2 Hz, 2H), 1.31 (t, J=7.2 Hz, 3H).

Provenance & Evidence