Stannous chloride dihydrate → HCID 58011019, compound

Participants

Reaction Conditions

Reaction Steps

N-(3-aminophenethyl)-2,2,2-trifluoroacetamide hydrochloride (0.27 g, 1.0 mmol) was suspended in 6M HCl (2.0 mL) and cooled thoroughly in an ice bath. This was rapidly stirred while a solution of NaNO2 (73 mg) in H2O (1.0 mL) was added slowly. The mixture was stirred at 0-5° C. for 45 min and was then treated with SnCl2.2H2O (1.3 g, 5.8 mmol) in 6N HCl (4.0 mL). The resulting suspension was stirred at 0-5° C. for 3 h and then carefully quenched with 3N NaOH (15 mL) to pH 7-8. The mixture was diluted with Et2O, filtered through Celite® and the filter cake was washed with H2O and Et2O. The layers of the biphasic filtrate were separated and the aqueous extracted with Et2O (2×). The combined organics extracts were washed with brine (1×), dried (Na2SO4), filtered and evaporated to provided N-(3-hydrazinophenethyl)-2,2,2-trifluoroacetamide as a pale yellow oil (0.18 g, 72% yield), which was used without further purification. MS (ESI) m/z: 248.0 (M+H+).

Provenance & Evidence