Methyl 3-aminocrotonate → 2-(N-benzyl-N-methylamino)ethyl methyl 2,6-dimethyl-4-(3-chloro-2-fluorophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

HRID 483196Notes

Reaction equation

HRID 483196 reaction equation
[Cl:1][C:2]1[C:3]([F:10])=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=O.[NH2:11]/[C:12](/[CH3:18])=[CH:13]\[C:14]([O:16][CH3:17])=[O:15].[C:19]([O:25][CH2:26][CH2:27][N:28]([CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[CH3:29])(=[O:24])[CH2:20][C:21]([CH3:23])=O>CC(O)C>[CH3:23][C:21]1[NH:11][C:12]([CH3:18])=[C:13]([C:14]([O:16][CH3:17])=[O:15])[CH:5]([C:4]2[CH:7]=[CH:8][CH:9]=[C:2]([Cl:1])[C:3]=2[F:10])[C:20]=1[C:19]([O:25][CH2:26][CH2:27][N:28]([CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[CH3:29])=[O:24]

Participants

5

Reactant 3

HCID 643918Methyl 3-aminocrotonateHCID 7363353-Chloro-2-fluorobenzaldehydeHCID 117768292-[Methyl(phenylmethyl)amino]ethyl 3-oxobutanoate

Product 1

HCID 103453292-(N-benzyl-N-methylamino)ethyl methyl 2,6-dimethyl-4-(3-chloro-2-fluorophenyl)-1,4-dihydropyridine-3,5-dicarboxylateYield 50.9%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 320 mg of 3-chloro-2-fluorobenzaldehyde, 252 mg of methyl 3-aminocrotonate and 510 mg of 2-(N-benzyl-N-methylamino)ethyl acetoacetate in 2 ml of 2-propanol was refluxed for 6 hours, and then the solvent was distilled off in vacuo. The residue was purified by the methods of a column chromatography on silica gel to yield 500 mg of the desired compound (106)

Workup

  1. temperaturewas refluxed for 6 hours
  2. distillationthe solvent was distilled off in vacuo
  3. customThe residue was purified by the methods of a column chromatography on silica gel

Sources & evidence

ORD record
ord-c9a8a53fc85c40d88eb5895ed9999b8d
Source dataset
uspto-grants-1986_03
Patent number
US04578395

Reaction notes

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