Chloroacetaldehyde → Hydrochloric Acid

Participants

Reaction Steps

To a solution of freshly prepared chloroacetaldehyde (2.30 g., 0.03 mole) in absolute ethanol (50 ml.) and water (12.5 ml.) was added a solution of 2-amino-3,4-dihydro-3,3-dimethyl-4-phenylquinolin-4-ol (6.66 g., 0.025 mole) in absolute alcohol (62.5 ml). Sodium bicarbonate (2.5 g) was added and the mixture refluxed for 6 hours. After cooling, a small precipitate was filtered off, and the filtrate concentrated in vacuo, taken up in water, extracted with ether, dried and evaporated. The residue was crystallised from isopropyl alcohol to give an intermediate (3.77 g., m.p. 188°-190° C). A solution of this intermediate in dried xylene (200 ml.) was refluxed under a Dean and Stark head for 21 hours, cooled and the xylene evaporated. The hydrochloride of the residue was recrystallised from isopropyl alcohol to give the title compound as its hydrochloride (2.4 g., 258°-260° C).

Provenance & Evidence