Ethyl Acetate → 6-Chloropyridine-2,3-diamine

Participants

Reaction Conditions

Reaction Steps

A flask was charged with 6-chloro-3-nitropyridin-2-amine (500 mg, 2.88 mmol) and tin(II) chloride dihydrate (3.25 g, 14.40 mmol) under argon. A 9:1 mixture of ethyl acetate:2-methyl-2-propanol was then added, and the reaction was allowed to stir at 60° C. for one hour. Sodium borohydride (55 mg, 1.44 mmol) was then added, and the reaction was allowed to stir for 3 hours at 60° C. The reaction mixture was then cooled and the solvent evaporated under reduced pressure. The solid was taken up in water and saturated aqueous sodium carbonate was added until pH˜7 was attained. The mixture was extracted with ethyl acetate (2×). The combined organics were washed with brine, and dried over magnesium sulfate. This mixture was filtered and the filtrate concentrated under reduced pressure. Recrystallization from ethyl acetate/hexanes afforded the title compound.

Provenance & Evidence