Stannous chloride dihydrate → (4-Amino-3-methylphenyl)(1-methyl-1H-imidazol-5-yl)methanone

Participants

Reaction Steps

A mixture of (1-methyl-1H-imidazol-5-yl)(3-methyl-4-nitrophenyl)methanone (3.3 g, 13.456 mmol, Intermediate 40: step b) and tin(II)chloride dihydrate (15.6 g, 67.282 mmol) in EtOH (80 mL) was stirred at reflux for 1 hour, cooled to room temperature overnight and evaporated in vacuo to remove most of the EtOH. The residue was poured into a 3M aqueous NaOH/ice solution rinsing with EtOAc. The mixture was stirred at room temperature for 15 minutes and layers were separated. The aqueous layer was again extracted with EtOAc. The combined EtOAc extracts were washed with brine, dried (Na2SO4), filtered, and evaporated in vacuo to provide crude product. The tan solid title compound was precipitated from Et2O, collected by filtration and dried.

Provenance & Evidence