3-Nitrobenzaldehyde → 2-Amino-6-dimethylamino-4-(3'-nitrophenyl)-4,5-dihydropyridine-3,5-dicarboxylic acid diethyl ester

HRID 1415293Notes

Reaction equation

HRID 1415293 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]([O:14][C:15](=[O:22])[CH:16]=[C:17]([N:19]([CH3:21])[CH3:20])[NH2:18])[CH3:13]>C(O)C>[CH2:12]([O:14][C:15]([C:16]1[CH:7]([C:6]2[CH:9]=[CH:10][CH:11]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[CH:16]([C:15]([O:14][CH2:12][CH3:13])=[O:22])[C:17]([N:19]([CH3:20])[CH3:21])=[N:18][C:17]=1[NH2:18])=[O:22])[CH3:13]

Participants

4

Reactant 2

HCID 74493-NitrobenzaldehydeHCID 867334643-Amino-3-dimethylaminoacrylic acid ethyl ester

Product 1

HCID 124486892-Amino-6-dimethylamino-4-(3'-nitrophenyl)-4,5-dihydropyridine-3,5-dicarboxylic acid diethyl ester

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

After boiling a solution of 7.5 g of 3-nitrobenzaldehyde and 15.8 g of N,N-dimethyl-3,3-diaminoacrylic acid ethyl ester in 150 ml of ethanol for 4 hours, the solution was concentrated in vacuo. On triturating the resulting oil with ether, filtering off the crystals which separated out and crystallizing these from isopropanol, the yellow-orange colored crystals of 2-amino-6-dimethylamino-4-(3'-nitrophenyl)-4,5-dihydropyridine-3,5-dicarboxylic acid diethyl ester, of melting point 149° C, were obtained. Yield, 61% of theory.

Workup

  1. customfor 4 hours
  2. concentrationthe solution was concentrated in vacuo
  3. customOn triturating the resulting oil with ether
  4. filtrationfiltering off the crystals which
  5. customseparated out
  6. customcrystallizing these from isopropanol

Sources & evidence

ORD record
ord-45286f4ad3ae4df6a81171266e5ac153
Source dataset
uspto-grants-1977_01
Patent number
US04004014

Reaction notes

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