Methyl vinyl ketone → 8-Fluoro-4-methylquinoline

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 2-fluoroaniline (1 g. 9.0 mmol.) in acetic acid (10 ml), activated silferc (1.4 g. ferric chloride 9.0 mmol) was added under nitrogen atmosphere. The reaction mixture was stirred for 5 minutes and methyl vinyl ketone (MVK) (0.7 g, 9.9 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 (1.2 g. 9.0 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 65%.

Provenance & Evidence