Ammonium Chloride → HCID 67261688, compound

Participants

Reaction Conditions

Reaction Steps

3-((3-Cyclopropyl-4-nitro-1H-indazol-1-yl)methyl)-1-methylpyridin-2(1H)-one (413 mg, 1.27 mmol) was dissolved in a mixture of ethanol (6.8 mL) and water (1.7 mL). Ammonium chloride (34 mg; 0.63 mmol) and iron powder (709 mg; 12.7 mmol) were added and the mixture was stirred with heating to 75° C. under a nitrogen atmosphere for 16 hours. The mixture was allowed to cool, diluted with ethyl acetate (50 mL) and filtered through a pad of Celite®. The filtrate was concentrated under reduced pressure to give the crude product as a colored oil. Purification using a silica gel preparative thin layer chromatography plate (20×20 cm, 2 mm) developed in a chamber with 40% ethyl acetate/dichloromethane, drying, and eluting with 80% ethyl acetate/dichloromethane gave 3-((4-amino-3-cyclopropyl-1H-indazol-1-yl)methyl)-1-methylpyridin-2(1H)-one as a viscous oil which began to crystallize upon drying under high vacuum (175 mg).

Provenance & Evidence