Hydrochloric Acid → HCID 21936548, compound

Participants

Reaction Conditions

Reaction Steps

(Method A) 4-Chloroaniline (2.55 g, 20 mmol), concentrated hydrochloric acid (5 cm3), tetrachloro-1-4-benzoquinone (5.9 g, 20 mmol), and n-butanol (5 cm3) were mixed and heated to reflux giving a yellow suspension. Crotonaldehyde (1.68 g, 24 mmol) in butanol (2 cm3) was added over 1 hr giving a dark brown solution. After a further 30 mins reflux, zinc chloride (0.5M in THF, 40 cm3, 20 mmol) was added in three portions and reflux continued for 20 mins before cooling slowly to 0° C. and standing for 1 hr. The dark solid was filtered off, washed with ether, IPA and THF before drying in vacuo to give 6-chloro-2-methylquinoline hydrochloride/zinc chloride salt (3 g, 10.6 mmol, 62%). See, for example, Song et al., 1993.

Provenance & Evidence