Nitrobenzene → HCID 20028938, compound

Participants

Reaction Steps

The starting material was prepared as follows. A solution of 4-amino-2-methylquinoline (5.0 g.) and allyl bromide (3.32 ml.) in nitrobenzene (13.7 ml.) was stirred at 100° for 1 hour. The reaction mixture was cooled to below 5° and the resulting precipitate filtered off, washed with ether and dried. A suspension of this material in N aqueous NaOH (75 ml.) was stirred at 100° for 3.5 hours. The cooled mixture was extracted with EtOAc (2×75 ml.) and the combined extracts washed, dried and evaporated to give 1-allyl-2-methyl-4-quinolone. Reaction of this compound with toluene-p-sulphonyl chloride gave 1-allyl-4-chloro-2-methylquinolinium toluene-p-sulphonate.

Provenance & Evidence