Methyl vinyl ketone → 8-Chloro-4-methylquinoline

Temperature

70 °C

To a stirred solution of 2-chloroaniline (1 g. 7.8 mmol.) in acetic acid (10 ml), activated silferc (1.25 g. ferric chloride 7.8 mmol) was added under nitrogen atmosphere. The reaction mixture was stirred for 5 minutes and methyl vinyl ketone (MVK) (0.6 g, 8.5 mmol) was added slowly over a period of 15 minutes. The reaction mixture was heated to 70° C. and maintained between 70-75° C. for one hour. Anhydrous zinc chloride (1.0 g. 7.8 mmol) was added and the reaction was further refluxed for two hours. The reaction mixture was cooled, filtered, basified with 10% NaOH solution, extracted with ethyl acetate (3×20 ml), dried over Na2SO4 and evaporated to give the product; Yield 62%.

1. temperaturemaintained between 70-75° C. for one hour
2. temperaturethe reaction was further refluxed for two hours
3. temperatureThe reaction mixture was cooled
4. filtrationfiltered
5. extractionextracted with ethyl acetate (3×20 ml)
6. dry with materialdried over Na2SO4
7. customevaporated
8. customto give the product

ORD record

ord-8d16e28f69ad4044a7a930d953541b53

Source dataset

uspto-grants-2010_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07692016B2