Water → 1-(7-Chloroquinazolin-4-yl)-5-methoxy-2-methylindol-3-ylacetic acid

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Reaction Steps

A mixture of acetaldehyde N1 -(7chloroquinazolin-4-yl)-p-methoxyphenylhydrazone hydrochloride (25g.) and laevulinic acid (50g.) in acetic acid (120ml.) was heated under reflux for 1-2 hours. The dark red mixture was then added to water (1.5 1.). The solid obtained was separated by filtration and dissolved in a mixture of water (50ml.) and 5N-aqueous ammonium hydroxide solution (50ml.). The solution was extracted with ether (3 × 50ml.) and the aqueous layer acidified with acetic acid to pH4. The mixture was then extracted with ethyl acetate (3 × 50ml.) and the extracts washed with water (30ml.) and then with saturated sodium chloride solution (30ml.) before being dried (MgSO4). Evaporation of the solvent gave a dark brown syrup which crystallised on addition of methanol (40ml.) to give 1-(7-chloroquinazolin-4-yl)5-methoxy-2-methylindol-3-ylacetic acid as a yellow solid, m.p. 205°-208° C.

Provenance & Evidence