Methylamine → Ethyl 6-chloro-4-(methylamino)pyridine-3-carboxylate

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Reaction Steps

To a solution of ethyl 4,6-dichloronicotinate (5 g, 22.8 mmol) in CH3CN (30 mL) was added dropwise aqueous methylamine (65%, 5.2 g, 45.6 mmol) at 0° C. The resulting mixture was stirred at RT for 8 h. The organic solution was removed under reduced pressure to give the crude product, which was suspended in H2O and extracted with EtOAc (3×20 mL). The combined extracts were washed with brine, dried (MgSO4) and concentrated to give ethyl 6-chloro-4-(methylamino)nicotinate (4 g, 82% yield), which was used in the next step without further purification. 1HNMR (300 MHz, DMSO-d6): δ 8.48 (s, 1 H), 8.04 (d, J=4.5 Hz, 1 H), 6.71 (s, 1 H), 4.27 (q, J=6.9 Hz, 2 H), 2.85 (d, J=5.1 Hz, 3 H), 1.29 (t, J=6.9 Hz, 3 H).

Provenance & Evidence