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

HRID 483195Notes

Reaction equation

HRID 483195 reaction equation
[F:1][C:2]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.[NH2:13]/[C:14](/[CH3:20])=[CH:15]\[C:16]([O:18][CH3:19])=[O:17].[C:21]([O:27][CH2:28][CH2:29][N:30]([CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[CH3:31])(=[O:26])[CH2:22][C:23]([CH3:25])=O>CC(O)C>[CH3:25][C:23]1[NH:13][C:14]([CH3:20])=[C:15]([C:16]([O:18][CH3:19])=[O:17])[CH:4]([C:3]2[CH:6]=[CH:7][CH:8]=[C:9]([N+:10]([O-:12])=[O:11])[C:2]=2[F:1])[C:22]=1[C:21]([O:27][CH2:28][CH2:29][N:30]([CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[CH3:31])=[O:26]

Participants

5

Reactant 3

HCID 643918Methyl 3-aminocrotonateHCID 104873252-Fluoro-3-nitrobenzaldehydeHCID 117768292-(Benzylmethylamino)ethyl acetoacetate

Product 1

HCID 104585422-(N-benzyl-N-methylamino)ethyl methyl 2,6-dimethyl-4-(2-fluoro-3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylateYield 50.7%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 330 mg of 2-fluoro-3-nitrobenzaldehyde, 252 mg of methyl 3-aminocrotonate and 506 mg of 2-(N-benzyl-N-methylamino)ethyl acetoacetate in 2 ml of 2-propanol was refluxed for 12 hours, and then the solvent was distilled off in vacuo. The residue was purified by the method of a column chromatography on silica gel to provide 492 mg of the desired compound (104).

Workup

  1. temperaturewas refluxed for 12 hours
  2. distillationthe solvent was distilled off in vacuo
  3. customThe residue was purified by the method of a column chromatography on silica gel

Sources & evidence

ORD record
ord-ea62279ae4f04ee9af0ad9ccf5f23c39
Source dataset
uspto-grants-1986_03
Patent number
US04578395

Reaction notes

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