Hydrochloric Acid → 2-Carboxymethyl-5-(3-chlorophenoxy)-1-(4-diethylaminophenyl)indole-3-carboxylic acid

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Reaction Steps

A mixture of 5-(3-chlorophenoxy)-1-(4-diethylaminophenyl)-2-ethoxycarbonylmethyl-indole-3-carboxylic acid ethyl ester (100 mg, 0.18 mmol, see step (a) above), NaOH (1 M in methanol, 2 mL, 2.0 mmol), NaOH (aq, 1 M, 2 mL, 2.0 mmol) and dioxane (2 mL) was stirred at reflux for 4 h, cooled, acidified to pH 4 with HCl (aq, 1 M) and extracted with EtOAc. The combined extracts were washed with H2O and brine, dried (Na2SO4), concentrated and purified by chromatography. Yield 50 mg (56%), mp 186-191° C.

Provenance & Evidence