Water → HCID 22105528, compound

Participants

Reaction Steps

Ethyl 4-[N-(2-benzyloxy-5-bromobenzyl)amino]3-nitrobenzoate (10 g) was dissolved in acetic acid (50 mL) (warming was required) and iron dust (6.92 g) was added followed by the addition of water (20 mL). There was an exothermic reaction (to 70° C.). The reaction mixture was stirred at ambient temperature for 16 hours, water (300 mL) was added and the mixture was extracted three times with ethyl acetate (100 mL each time). The combined extracts were washed consecutively with water (3×100 mL) and saturated aqueous sodium bicarbonate (2×100 mL) and dried (MgSO4). The residue obtained on removal of the solvent was filtered through silica, eluting initially with a mixture of dichloromethane and hexane (1/1 v/v) and then with dichloromethane, to give ethyl 4-[N-(2-benzyloxy-5-bromobenzyl)amino]-3-aminobenzoate, yield 8.78 g, mp 135° C.

Provenance & Evidence