4-Methoxybenzylamine → Ethyl 4-(4-methoxybenzylamino)-6-chloropyridine-3-carboxylate

Participants

Reaction Steps

Stir a mixture of ethyl 4,6-dichloronicotinate (16 g, 73.1 mmol), (4-methoxybenzyl)amine (10 g, 73.1 mmol), and TEA (15.2 g, 146 mmol) in DMSO (150 mL) at RT overnight. Add EtOAc, wash with water (2×), then brine (1×), dry the organics over MgSO4 and concentrate to afford the title compound (21 g, 90%). 1H NMR (300 MHz, CDCl3): δ 8.62 (s, 1H), 8.39 (s, 1H), 7.16 (d, J=8.7 Hz, 2H), 6.85-6.80 (m, 2H), 6.49 (s, 1H), 4.33-4.25 (m, 4H), 3.77 (s, 3H), 1.31 (t, J=6.9 Hz, 3H).

Provenance & Evidence