2-Hydroxyquinoline → HCID 23342064, compound

Participants

Reaction Steps

3.28 g of 5-(1-hydroxy-2-isopropylaminobutyl)-8-hydroxy-3,4-dihydrocarbostyril hydrochloride was dissolved in 50 ml of methanol, and a 20% methanolic solution of sodium methylate was added to the solution in an amount of 2 moles per mole of the starting carbostyril compound. The mixture was then concentrated to dryness, and the residue was dissolved in dimethylformamide. 1.7 g of p-toluylic acid chloride was added to the solution while cooling with ice-water and the mixture was stirred for 4 hours at room temperature. The reaction mixture was poured into ice-water and extracted with chloroform. A mixture of diethyl ether and petroleum benzene was added to the chloroform extract to obtain 1.94 g of crystalline 5-(1-hydroxy-2-isopropylaminobutyl)-8-p-methylbenzoyloxy-3,4-dihydrocarbostyril having a melting point of 151.5°-152.5° C. (after recrystallization from chloroform-n-hexane).

Provenance & Evidence