Methyl 3-aminocrotonate → 2-Methyl-6-(3-trifluoromethyl-phenyl)-nicotinic Acid Methyl Ester
Reaction equation
Cl.CN(C)[CH2:4][CH2:5][C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=1)=O.[CH3:19][O:20][C:21](=[O:26])/[CH:22]=[C:23](\[NH2:25])/[CH3:24]>CC(O)=O>[CH3:19][O:20][C:21](=[O:26])[C:22]1[CH:4]=[CH:5][C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:15])([F:16])[F:17])[CH:9]=2)=[N:25][C:23]=1[CH3:24]Participants
4
Procedure
5.57 g (19.76 mmol) of the above prepared 3-dimethylamino-1-(3-trifluoromethyl-phenyl)-propan-1-one hydrochloride and 2.28 g (1.00 eq.) of 3-aminocrotonic acid methyl ester were dissolved in 60 ml of AcOH and heated to reflux for 4 h. After cooling, the bulk of the solvent was evaporated i. V., the residue dissolved in AcOEt and washed with water and brine. Drying over sodium sulfate, evaporation of the solvents and flash chromatography (SiO2, hexane/AcOEt=89/11) delivered finally 2.00 g of the title compound as light yellow crystals of mp. 47-49° C. (dec.).