Potassium tert-butoxide → Ethyl 1-cyclohexyl-7-iodo-4-oxo-1,4-dihydro-quinoline-3-carboxylate
Reaktionsgleichung
Cl[C:2]1[CH:23]=[C:22]([I:24])[CH:21]=[CH:20][C:3]=1[C:4]([C:6](=[CH:12][NH:13][CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)[C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:5].CC([O-])(C)C.[K+]>CS(C)=O>[CH:14]1([N:13]2[C:20]3[C:3](=[CH:2][CH:23]=[C:22]([I:24])[CH:21]=3)[C:4](=[O:5])[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:12]2)[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
mg) A suspension of 17.8 g of ethyl 2-(2-chloro-4-iodo-benzoyl)-3-cyclohexylamino-acrylate in 150 ml of dimethyl sulphoxide is treated portionwise at room temperature while stirring with 4.75 g of potassium tert-butylate and the mixture is subsequently heated at 50° for 1 hr. The mixture is left to cool to room temperature, poured into 500 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 1-cyclohexyl-7-iodo-4-oxo-1,4-dihydro-quinoline-3-carboxylate as a colourless solid. M.p. 169°-171° C.