O-Phenylenediamine → HCID 19867715, compound

Participants

Reaction Steps

2-Methoxy-8-methylquinoline-6-carboxylic acid (1.09 g) was added in portions to a stirred mixture of o-phenylene diamine (0.54 g) and phosphorus oxychloride (20 cm3) at room temperature (20° ). The mixture was heated under reflux for 4 hours and then solvent was evaporated in vacuo. Ice (20 g) was added to the residue which was then basified to pH 9 with aqueous 2.5M sodium hydroxide and filtered to yield a solid which was chromatographed on silica (Merck "MK 60.9385" [Trade Mark]) eluting with methanol:dichloromethane, 1:100 by volume. Combination and evaporation of appropriate fractions gave the title compound which was characterised spectroscopically and used directly in Example 2 without further purification.

Provenance & Evidence