Hydrochloric Acid → 3-(Aminomethyl)-5-bromopyridine

Participants

Reaction Steps

To the cobalt chloride hexahydrate (71 mg, 0.55 mmol) and 5-bromonicotinonitrile (Aldrich, 1 g, 5.5 mmol) in THF:water (19.5:9.25 ml) at 0° C., Sodium borohydride (416 mg, 11.0 mmol) was added in portions with intermittent cooling of the reaction mixture. Once all the sodium borohydride was added, the reaction mixture was stirred for RT for 2 h. Then the reaction mixture was acidified with 3N HCl and stirred at RT for 3.5 h. Then THF was removed under vacuum and the aqueous layer was extracted with ether and ethereal layer was discarded. Then aqueous layer was basified with aqueous NH4OH solution and extracted repeatedly with CHCl3 (3×100 ml). Organic layer was dried on anhydrous sodium sulfate and volatiles were removed under vacuum. Column chromatography (MeOH/CHCl3: 3/97) of the crude residue resulted in (5-bromopyridin-3-yl)methanamine in 25% yield.

Provenance & Evidence