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

HRID 483194Notes

Reaction equation

HRID 483194 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

4

Reactant 3

HCID 357452,3-DichlorobenzaldehydeHCID 643918Methyl 3-aminocrotonateHCID 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.

Workup

  1. temperatureThe mixture was refluxed for 12 hours
  2. distillationThe solvent was distilled off in vacuo
  3. customthe residue was chromatographed over silica gel with a mixture of chloroform and ethyl acetate
  4. washas eluting solvents

Sources & evidence

ORD record
ord-1f203e0e35ac4dd28b6d8fe6df55c2c7
Source dataset
uspto-grants-1986_03
Patent number
US04578395

Reaction notes

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