Acetic Acid → HCID 22105524, compound

Participants

Reaction Steps

5-Bromo-2-benzyloxybenzaldehyde (7.2 g) and ethyl 2-[4-aminophenyl]acetate (4.45 g) were heated on a steam bath for 2 hours. The mixture was cooled and dissolved in ethanol (100 ml) and NaBH4 (0.94 g) was added. The mixture was stirred at ambient temperature for 30 minutes, NaBH4 (0.5 g) added and stirred at ambient temperature for 2 hours. Acetic acid (2 ml) was added dropwise and the solvent evaporated to half volume. The mixture was partitioned between water (100 ml) and diethyl ether (3×75 ml) and the combined organic extracts washed with NaHCO3 (2×50 ml), dried (MgSO4) and evaporated. The residue was subjected to chromatography eluting with CH2Cl2 to give ethyl 2-[4-(2-benzyloxy-5-bromobenzylamino)phenyl]acetate: (yield 6.4 g, m.p. 73° C.).

Provenance & Evidence