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3-Nitrobenzaldehyde → 3-(1-Benzylpyrrolidin-3-yl) 5-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

HRID 2211234
Notes
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Reaction equation

HRID 2211234 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH:7]=O)([O-:3])=[O:2].[CH2:12]([N:19]1[CH2:23][CH2:22][CH:21]([O:24][C:25](=[O:30])[CH2:26][C:27]([CH3:29])=O)[CH2:20]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[CH3:31][O:32][C:33](=[O:38])/[CH:34]=[C:35](\[NH2:37])/[CH3:36]>C(O)(C)C.C(Cl)(Cl)Cl>[CH3:31][O:32][C:33]([C:34]1[CH:7]([C:6]2[CH:9]=[CH:10][CH:11]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[C:26]([C:25]([O:24][CH:21]2[CH2:22][CH2:23][N:19]([CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:20]2)=[O:30])=[C:27]([CH3:29])[NH:37][C:35]=1[CH3:36])=[O:38]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 74493-NitrobenzaldehydeHCID 643918Methyl 3-aminocrotonateHCID 136528121-Benzyl-3-acetoacetoxypyrrolidine

Product 1

HCID 22963-(1-Benzylpyrrolidin-3-yl) 5-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylateYield 99.9%

Reagents, catalysts & solvents 2

HCID 3776
Isopropanol
Solvent
HCID 6212ChloroformSolvent

Procedure

In 5 ml of isopropanol were dissolved 1.51 g (0.01 mole) of 3-nitrobenzaldehyde, 2.61 g (0.01 mole) of 1-benzyl-3-acetoacetoxypyrrolidine, and 1.15 g (0.01 mole) of 3-aminocrotonic acid methyl ester and the solution thus obtained was refluxed for 8 hours. Then, the solvent was distilled off under reduced pressure, the residue thus formed was dissolved in chloroform, the solution was washed, in succession, with diluted hydrochloric acid, water, a saturated aqueous sodium hydrogencarbonate solution, and dried over anhydrous magnesium sulfate. Then, the solvent was distilled off under reduced pressure to provide 4.91 g of 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-(1-benzylpyrrolidin-3-yl)ester 5-methyl ester as a caramel form.

Workup

  1. customthe solution thus obtained
  2. temperaturewas refluxed for 8 hours
  3. distillationThen, the solvent was distilled off under reduced pressure
  4. customthe residue thus formed
  5. washthe solution was washed, in succession, with diluted hydrochloric acid, water
  6. dry with materiala saturated aqueous sodium hydrogencarbonate solution, and dried over anhydrous magnesium sulfate
  7. distillationThen, the solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-c2bd1187a86e4a06b74c5a2f9107eb03
Source dataset
uspto-grants-1995_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05463064

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes