Sodium Bicarbonate → Methyl 4-(5-aminobenzo[b]thien-3-ylmethyl)-3-methoxybenzoate

Participants

Reaction Steps

Stannous chloride dihydrate (0.38 g.) was added to a stirred solution of (I) (0.12 g.) in ethanol (5 ml.), under an atmosphere of nitrogen. The mixture was heated under reflux for 2 hours. The cooled mixture was basified with saturated aqueous sodium bicarbonate (15 ml.) and extracted with ethyl acetate (2×25 ml.). The extracts were dried (MgSO4) and evaporated. The residual oil was purified by flash chromatography on silica gel (50 ml.), eluting with 3:7 v/v ethyl acetate:hexane to give methyl 4-(5-aminobenzo[b]thien-3-ylmethyl)-3-methoxybenzoate (H) (0.06 g., 54%) as an oil: NMR (80 MHz, DMSO-d6): 3.84 (s,3 H, OCH3), 3.91 (s,3 H, OCH3), 4.03 (s,2 H, CH2 --Ar), 5.0 (br s,2 H, NH2), 6.80 (m,2 H), 7.14 (m,2 H), 7.52 (m,3 H).

Provenance & Evidence