Methyl vinyl ketone → 4,8-Dimethylquinoline

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 2-methylaniline (1 g. 9.3 mmol.) in acetic acid (10 ml), activated silferc (1.5 g., ferric chloride 9.3 mmol) was added under nitrogen atmosphere. The reaction mixture was stirred for 5 minutes and methyl vinyl ketone (MVK) (0.72 g, 10.2 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 (1.27 g. 9.3 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