Hydrochloric Acid → HCID 12782121, compound

Participants

Reaction Steps

This tetrahydroquinolinone is dissolved in 100 ml of dimethylformamide/toluene (1:1); after addition of 1.8 g of sodium hydride (80% in paraffin oil), stirring is effected for 30 minutes at room temperature, followed by addition of 7.8 g of dimethyl sulphate and heating to 50° for 1 hour. After cooling of the mixture, 600 ml of water and 20 ml of 2 N sodium hydroxide solution are added; stirring is effected for 10 minutes, followed by acidification with 2 N hydrochloric acid. Extraction with ethyl acetate (4 times, with 300 ml each time), drying and concentration yield a solid residue which is recrystallised from ethyl acetate/petroleum ether (1:1) and yields 6.0 g (55% of theory) of 6-chloro-1-methyl-1,2,3,4-tetrahydroquinolin-2-one (m.p. 76°-78° C.).

Provenance & Evidence