m-Formylbenzonitrile → HCID 68121126, compound

HRID 1283287Notes

Reaction equation

HRID 1283287 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH:6]=O)#[N:2].[CH2:11]([O:13][C:14](=[O:22])[CH2:15][C:16]([CH2:18][O:19][CH2:20][CH3:21])=O)[CH3:12].[CH2:23]([O:25][C:26](=[O:32])[CH:27]=[C:28]([NH2:31])[CH2:29][CH3:30])[CH3:24]>C(O)C>[CH2:11]([O:13][C:14]([C:15]1[CH:6]([C:5]2[CH:8]=[CH:9][CH:10]=[C:3]([C:1]#[N:2])[CH:4]=2)[C:27]([C:26]([O:25][CH2:23][CH3:24])=[O:32])=[C:28]([CH2:29][CH3:30])[NH:31][C:16]=1[CH2:18][O:19][CH2:20][CH3:21])=[O:22])[CH3:12]

Participants

5

Reactant 3

HCID 90670m-FormylbenzonitrileHCID 3016245Ethyl 4-ethoxy-3-oxobutyrateHCID 71322013HCID 71322013, compound

Product 1

HCID 68121126HCID 68121126, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

6.5 g of 3-cyanobenzaldehyde, 8.7 g of γ-ethoxyaceto-acetic acid ethyl ester and 7.2 g of β-amino-β-ethylacrylic acid ethyl ester in 80 ml of ethanol are heated overnight under reflux, the mixture is cooled, and after filtration, and washing with cold ethanol, 2-ethoxymethyl-6-ethyl-4-(3'-cyanophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid diethyl ester is obtained in the form of light yellow crystals of melting point 125°C, in a yield of 42% of theory.

Workup

  1. temperatureunder reflux
  2. temperaturethe mixture is cooled
  3. filtrationafter filtration
  4. washwashing with cold ethanol

Sources & evidence

ORD record
ord-69808e8dff2b45b09ca22e37924fd607
Source dataset
uspto-grants-1976_08
Patent number
US03974278

Reaction notes

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