3-Nitrobenzaldehyde → 2,6-Dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid

HRID 2418261Notes

Reaction equation

HRID 2418261 reaction equation
[C:1]([O-:7])(=[O:6])[CH2:2][C:3]([CH3:5])=O.[N+:8]([C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=1)[CH:14]=O)([O-:10])=[O:9].N1CCCCC1.[NH2:25]/[C:26](/[CH3:31])=[CH:27]\[C:28]([O-:30])=[O:29]>C1C=CC=CC=1>[CH3:5][C:3]1[NH:25][C:26]([CH3:31])=[C:27]([C:28]([OH:30])=[O:29])[CH:14]([C:13]2[CH:16]=[CH:17][CH:18]=[C:11]([N+:8]([O-:10])=[O:9])[CH:12]=2)[C:2]=1[C:1]([OH:7])=[O:6]

Participants

6

Reactant 4

HCID 74493-NitrobenzaldehydeHCID 8082PiperidineHCID 6971017AcetoacetateHCID 222503863-Aminocrotonate

Product 1

HCID 133631442,6-Dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acidYield 34.4%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

In 50 ml of benzene were dissolved 4 g of 2-nitratopropyl acetoacetate, 2.9 g of 3-nitrobenzaldehyde and 0.3 ml of piperidine. The solution was subjected to reflux, extraction, washing, dryness and evaporation of the solvent in the manner described in Example 9 to give a residue, to which 3.5 g of 2-nitratoethyl 3-aminocrotonate was then added. The mixture was treated in the manner described in Example 9 to give a residue, which was then subjected to column chromatography on silica gel (eluted with n-hexane-ethyl acetate=2:1) and recrystallized from ether to obtain 2.1 g of 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-(2-nitratoethyl) ester-5-(2-nitratopropyl) ester.

Workup

  1. temperatureto reflux
  2. extractionextraction
  3. washwashing
  4. customdryness and evaporation of the solvent in the manner
  5. customto give a residue
  6. additionThe mixture was treated in the manner
  7. customto give a residue, which
  8. customrecrystallized from ether

Sources & evidence

ORD record
ord-6bcccfdf14d740eb8dbd9bdb27bca8a8
Source dataset
uspto-grants-1984_09
Patent number
US04472411

Reaction notes

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