Ammonia → HCID 86718216, compound

Participants

Reaction Steps

Under argon, 29.8 g (105.1 mmol) of 5-chloro-3-[(3-fluoropyridin-2-yl)methoxy]-2-nitropyridine from Example 126A were initially charged in 317 ml of ethanol. 18.2 g (325.7 mmol) of iron powder were added, and the reaction mixture was heated to reflux. 80.4 ml of conc. hydrochloric acid were slowly added dropwise, and the mixture was heated under reflux for a further 6 h. The reaction mixture was made alkaline with 33% strength aqueous ammonia solution and then concentrated under reduced pressure. Purification by silica gel chromatography (mobile phase: dichloromethane/methanol gradient: 95/5 to 90/10) gave 25.0 g (94% of theory) of the target compound.

Provenance & Evidence