2,3-Dichlorobenzaldehyde → 2-(N-benzyl-N-methylamino)ethyl methyl 2,6-dimethyl-4-(2,3-dichlorophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

Reaction equation

[Cl:1][C:2]1[C:9]([Cl:10])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.[C:11]([O:17][CH2:18][CH2:19][N:20]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH3:21])(=[O:16])[CH2:12][C:13]([CH3:15])=O.[NH2:29]/[C:30](/[CH3:36])=[CH:31]\[C:32]([O:34][CH3:35])=[O:33]>>[CH3:15][C:13]1[NH:29][C:30]([CH3:36])=[C:31]([C:32]([O:34][CH3:35])=[O:33])[CH:4]([C:3]2[CH:6]=[CH:7][CH:8]=[C:9]([Cl:10])[C:2]=2[Cl:1])[C:12]=1[C:11]([O:17][CH2:18][CH2:19][N:20]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH3:21])=[O:16]

Participants

Reactant 3

HCID 357452,3-Dichlorobenzaldehyde

HCID 643918Methyl 3-aminocrotonate

HCID 117768292-(Benzylmethylamino)ethyl acetoacetate

Product 1

HCID 104811922-(N-benzyl-N-methylamino)ethyl methyl 2,6-dimethyl-4-(2,3-dichlorophenyl)-1,4-dihydropyridine-3,5-dicarboxylateYield 59.6%

Procedure

To a solution of 350 mg of 2,3-dichlorobenzaldehyde in 2 ml of 2-prapanol were added 510 mg of 2-(N-benzyl-N-methylamino)ethyl acetoacetate and 250 mg of methyl 3-aminocrotonate. The mixture was refluxed for 12 hours. The solvent was distilled off in vacuo, and then the residue was chromatographed over silica gel with a mixture of chloroform and ethyl acetate as eluting solvents to yield 600 mg of the desired compound. The physical properties are as follows.