Tin tetrachloride dihydrate → HCID 68651299, compound

Participants

Reaction Steps

5-(2-thienyl)-2,3-dihydro-1H-indene-1-yl)amine: To a solution of 2-(1-azido-2,3-dihydro-1H-indene-5-yl)thiophene (0.24 g, 0.99 mmol) in methanol (2mL) was added solid tin chloride dihydrate (0.45 g, 1.99 mmol) at room temperature under nitrogen. The reaction was stirred at room temperature overnight. The crude reaction mixture was poured into a separatory funnel and diluted with ethyl acetate (250 mL). The organic layer was washed with 2.0 N aqueous sodium hydroxide (50 mL), saturated aqueous sodium chloride (brine), and dried over anhydrous magnesium sulfate. Filtration, concentration and column chromatography on silica (9:1 dichloromethane/methanol) gave [5-(2-thienyl)-2,3-dihydro-1H-indene-1-yl]amine (0.15 g, 72% yield) as semi-solid: 1H NMR (400 MHz, CDCl3) 7.54 (m, 1H), 7.40 (d, 2H), 7.29 (m, 2H), 7.08 (m, 1H), 4.40 (t, 1H), 3.05 (m, 1H), 2.90 (m, 1H), 2.56 (m, 1H), 1.80 (m, 1H).

Provenance & Evidence