Cyclohexylamine → HCID 19081700, compound

Participants

Reaction Steps

13ad) A solution of 20 g of ethyl 2-(4-bromo-2-chloro-benzoyl)-3-dimethylaminoacrylate (Example 13ac)) in 200 ml of dimethyl sulphoxide is treated with 5.5 g of cyclohexylamine and stirred at room temperature under argon for 45 min. Immediately after the addition the solution begins to decolourize and a colourless, gel-like substance separates. 6.84 g of potassium tert-butylate are added in one portion to this suspension. The resulting suspension is stirred at room temperature for 10 min. and subsequently heated to 50° for 1.5 hrs. The reaction mixture is left to cool to room temperature, poured into 600 ml of ice-water and stirred for a further 30 min. The suspension is suction filtered, the filter residue is washed three times with 100 ml of water each time and three times with 100 ml of hexane each time and dried. Recrystallization of the crude product from ethyl acetate/hexane yields 14.8 g (90%) of ethyl 7-bromo-1-cyclohexyl-4-oxo-1,4-dihydro-quinoline-3-carboxylate as a colourless solid. M.p. 129°-133°.

Provenance & Evidence