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

HRID 2418259Notes

Reaction equation

HRID 2418259 reaction equation
[C:1]([O-:7])(=[O:6])[CH2:2][C:3]([CH3:5])=O.[NH2:8]/[C:9](/[CH3:14])=[CH:10]\[C:11]([O-:13])=[O:12].[N+:15]([C:18]1[CH:19]=[C:20]([CH:23]=[CH:24][CH:25]=1)[CH:21]=O)([O-:17])=[O:16]>C(O)(C)C>[CH3:5][C:3]1[NH:8][C:9]([CH3:14])=[C:10]([C:11]([OH:13])=[O:12])[CH:21]([C:20]2[CH:23]=[CH:24][CH:25]=[C:18]([N+:15]([O-:17])=[O:16])[CH:19]=2)[C:2]=1[C:1]([OH:7])=[O:6]

Participants

5

Reactant 3

HCID 74493-NitrobenzaldehydeHCID 6971017AcetoacetateHCID 222503863-Aminocrotonate

Product 1

HCID 133631442,6-Dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acidYield 73.3%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

In 30 ml of isopropyl alcohol were dissolved 1.1 g of 2-nitratopropyl acetoacetate, 1.1 g of 3-nitratopropyl 3-aminocrotonate and 0.79 g of 3-nitrobenzaldehyde. The solution was treated in the manner described in Example 1 to obtain a residue, which was then subjected to column chromatography on silica gel (eluted with n-hexane-ethyl acetate=5:1) and recrystallized from ether to obtain 1.22 g of 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-(2-nitratopropyl) ester-5-(3-nitratopropyl) ester.

Workup

  1. additionThe solution was treated in the manner
  2. customto obtain a residue, which
  3. customrecrystallized from ether

Sources & evidence

ORD record
ord-6b91cbe6ced3436ea204bf8d797438a5
Source dataset
uspto-grants-1984_09
Patent number
US04472411

Reaction notes

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