Phosphoric Acid → HCID 70607362, compound

Participants

Reaction Steps

A solution of 5,6-dimethoxy-2,4-dimethyl-8-[(4-phthalimidopentyl)-amino]quinoline (12.7 g, 28 mmole) in ethanol (270 ml) containing 75% hydrazine (5.6 g, 84 mmole) was refluxed for 18 hr. An additional portion of 75% hydrazine (1.0 g, 15 mmole) was added and the mixture was refluxed for 1 hr more. Following the usual work-up, the base was isolated as a yellow-orange oil. The oil was dissolved in ethanol (30 ml) and treated dropwise with 0.90 equiv (27.8 ml) of 1 M phosphoric acid in ethanol. The phosphate salt separated initially as a gum, but dilution with ether (300 ml), seeding, and thorough trituration for several hours gave a uniform yellow solid, 11.5 g (90%), mp 163°-166°. Crystallization of the crude phosphate from methanol-ethanol-ether (1:1:2) afforded 82% recovery of product; mp 163°-166°.

Provenance & Evidence