Hydrochloric Acid → HCID 178424849, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 7-(2,5-dimethylphenyl)-4-methyl-5,6,7,8-tetrahydroquinolin-5-one (100 mg), 1-amino-3-hydroxyguanidine p-toluenesulfonate (131 mg) and concentrated hydrochloric acid (0.1 ml) in ethanol (2 ml) was stirred at 85° C. (bath temperature) for 1 hour. The reaction solution was concentrated under reduced pressure, and to the residue were added ethyl acetate (20 ml), tetrahydrofuran (12 ml) and 0.2 N sodium hydroxide (10 ml). The mixture was shaken, and the separated upper layer was washed with 0.2 N sodium hydroxide (5 ml) and water (5 ml, thrice). To the upper layer was added 2 N hydrochloric acid (0.5 ml), and the mixture was concentrated under reduced pressure. The residue was washed with a mixture of ether (4 ml) and ethanol (2 ml), and dried to give 7-(2,5-dimethylphenyl)-5-(1-hydroxyguanidin-3-yl)imino-4-methyl-5,6,7,8-tetrahydroquinoline hydrochloride (Compound 94) (121 mg) as yellow crystals.

Provenance & Evidence