Methanol → (5-Chloropyridin-2-yl)methanamine hydrochloride

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Reaction Steps

The compound 2-(aminomethyl)-5-chloropyridine (18 g, 0.13 mol, from Step D) was dissolved in dichloromethane (50 mL) and hydrochloric methanol solution (5 M, 50 mL) was added. After stirring for several min a white solid began to precipitate. The mixture was stirred for 1 h at 0-5° C., and the solid was collected by filtration and the filtrate was evaporated in vacuo to give some off-white solid. The combined solid was washed with a small amount of cold DCM. The product was dried in vacuo to yield the indicated compound as the hydrochloric salt. 1H-NMR (DMSO-d6, 400 MHz) δ 8.70 (s, 3H), 8.62 (s, 1H), 8.0 (dd, J=2.5, 6 Hz, 1H), 7.60 (d, J=8.5 Hz, 1H), 4.15 (m, 2H).

Provenance & Evidence