HCID 178418361, compound → HCID 178439523, compound

Participants

Reaction Steps

A solution of 49.0 parts of ethyl 3-allyl-4-hydroxy-quinoline-2-carboxylate in 600 parts of boiling ethanol was stirred for 5 minutes in 3 parts of 3% palladium-on-carbon catalyst, then filtered and the filtrate together with 5 parts of fresh catalyst was charged to a stainless steel autoclave and hydrogen added at room temperature to a pressure of 50 atmospheres. After stirring at 16 hours 1.38 moles of hydrogen had been absorbed. The reaction mixture was dissolved in hot ethanol, filtered to remove catalyst, and evaporated to give 39.3 parts of ethyl 3-n-propyl-4-hydroxyquinoline-2-carboxylate, pale yellow needles, m.pt. 155°-157°C which were collected and dried; a further 4.8 parts of less pure product m.pt. 140°-146°C were recovered from the ethanolic mother liquors after concentration in vacuo. After repeated recrystallisation from ethanol very pale yellow prismatic needles, m.pt. 158°-159.5°C were obtained. (Found: C 69.3; H 6.3; N 5.2%. C15H17NO3 requires C 69.5; H 6.6; N 5.4%).

Provenance & Evidence