Hydrochloric Acid → HCID 74041496, compound

Participants

Reaction Steps

1-(2-Benzyloxyethyl)-2-oxo-6-propionyl-1,2,3,4-tetrahydroquinoline (32.4 g) was dissolved in methylene chloride (97 ml) and the solution was saturated with hydrogen chloride. To the stirred solution was added dropwise iso-amyl nitrite (13.5 g) over 0.5 hour. After stirring for 1 hour, the reaction mixture was evaporated in vacuo and the oily residue was dissolved in diethyl ether and extracted with 10% aqueous solution of sodium hydroxide. The extract was washed with diethyl ether, acidified with diluted hydrochloric acid, and extracted with chloroform. The extract was washed with water, dried over magnesium sulfate, and evaporated in vacuo. The oily residue was triturated with benzene to give 1-(2-benzyloxyethyl)-6-(2-hydroxyiminopropionyl)-2-oxo-1,2,3,4-tetrahydroquinoline (9.19 g).

Provenance & Evidence