4-methoxy-2-n-propylpyridine-N-oxide → 4-Methoxy-2-n-propylpyridine

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Reaction Conditions

Reaction Steps

A solution of 4-methoxy-2-n-propylpyridine-N-oxide (59.3 g, 0.355 mol) in 800 ml of 1 M sulfuric acid was stirred and heated to 70-80° C. Zinc dust (140.0 g, 214 mol) was added in portions over four hours. When the addition was complete, heating was continued for a further eight hours. The resulting precipitate was filtered off and washed with water. The filtrate was made strongly alkaline by addition of a 32% sodium hydroxide solution and extracted with dichloromethane (3×250 ml). The extracts were combined, dried with sodium sulfate, filtered and evaporated to a yellow oil. Distillation (0.1-0.2 mbar, 44-46° C.) afforded 46.1 g (86%) of 4-methoxy-2-n-propylpyridine as a colourless oil. 1H-NMR (CDCl3, 200 MHz) δ: 0.99 (t, 3H), 1.75 (sext, 2H), 2.72 (t, 2H), 3.81 (s, 3H), 6.10-6.18 (m, 2H), 8.35 (d, 1H).

Provenance & Evidence