Stannous Chloride → Ethyl 3-(3-aminophenyl)pyridine-4-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-(3-nitrophenyl)-4-pyridinecarboxyiic acid ethyl ester in ethyl acetate (20 mL) was added tin(II) chloride (1.47 g). The mixture was heated at 80° C. for 45 min, then allowed to cool to ambient temperature. The mixture was poured into ice and saturated aqueous sodium bicarbonate was added until the mixture attained a pH of approximately 7. Celite and ethyl acetate were added, and the mixture was stirred for 10 min. The mixture was filtered and placed in a separatory funnel. The organic layer was separated, dried over sodium sulfate, filtered and concentrated to yield the crude product. Purification by silica gel chromatography (4:1 hexane: ethyl acetate) afforded the title compound as an orange oil (216 mg).

Provenance & Evidence