Ammonia → 3-Aminopyridine-2-carbonitrile

Participants

Reaction Conditions

Reaction Steps

A solution of 3-fluoro-2-cyanopyridine (Sakamoto et. al., Chem. Pharm. Bull. 1985, 33: 565-571) (10 g, 82 mmol) in DMSO (30 mL) was placed in a pressure vessel and saturated with ammonia gas. The reaction was capped and heated to 70 degrees C. overnight. The reaction was cooled, vented and re-saturated with ammonia, then sealed and re-heated for several hours. The reaction was cooled, vented, diluted with CHCl3 and the solids that had formed were filtered off. The solution was added to the top of a silica gel column (150 mm×7 inches) saturated with CHCl3 and the column was eluted with a gradient of 100% CHCl3 to 100% CHCl3 saturated with NH3. The fractions were collected and concentrated to give the product which contained some residual DMSO. This was used a in the next step.

Provenance & Evidence