Triethylamine → 1-cyclohexylmethyl-7-methoxy-1H-indole-3-carboxylic acid N'-(2-chloroacetyl)hydrazide

Participants

Reaction Steps

To a suspension of 1-cyclohexylmethyl-7-methoxy-1H-indole-3-carboxylic acid (1.0 g, 3.48 mmol) in dichloromethane (20 ml) was added oxalyl chloride (0.6 ml, 6.96 mmol) and the reaction stirred for 3.5 h. The solvent was evaporated under reduced pressure and the resulting residue redissolved in dichloromethane (20 ml). To the solution was added chloroacetic acid hydrazide (1.3 g, 8.97 mmol) and triethylamine (2.9 ml, 20.9 mmol) and the reaction mixture stirred for 4 h and then left to stand overnight. The solvent was evaporated under reduced pressure and the resulting residue purified by flash column chromatography eluting with 50-100% (v/v) ethyl acetate in heptane to give 1-cyclohexylmethyl-7-methoxy-1H-indole-3-carboxylic acid N′-(2-chloroacetyl)hydrazide (397 mg, 1.05 mmol).

Provenance & Evidence