2-(Chloromethyl)-3,5-dimethyl-4-methoxypyridine hydrochloride → (4-Methoxy-3,5-dimethylpyridin-2-yl)methanamine

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Reaction Steps

A solution of 2-chloromethyl-4-methoxy-3,5-dimethyl-pyridine HCl (Aldrich 3.7 g, 16.6 mmole) in 7N NH3/MeOH (Aldrich, 200 mLs) was refluxed in a steel bomb for 15 hours. Removed the solvent under reduced pressure, the residue was taken into 5% MeOH/CH2Cl2 and filtering it through a thin layer of silica gel afforded the product at 76% yield. HPLC RT was 2.850 min. 1HNMR (CDCl3) δ 8.18 (s, 1H), 4.32 (s, 2H), 3.76 (s, 3H), 2.23 (s, 3H), 2.18 (s, 3H).

Provenance & Evidence