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

HRID 2418257Notes

Reaction equation

HRID 2418257 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:25]=[CH:24][CH:23]=[CH:22][C:19]=1[CH:20]=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:20]([C:19]2[CH:22]=[CH:23][CH:24]=[CH:25][C:18]=2[N+:15]([O-:17])=[O:16])[C:2]=1[C:1]([OH:7])=[O:6]

Participants

5

Reactant 3

HCID 111012-NitrobenzaldehydeHCID 6971017AcetoacetateHCID 222503863-Aminocrotonate

Product 1

HCID 120733112,6-Dimethyl-3,5-dicarboxy-4-(2-nitrophenyl)-1,4-dihydropyridineYield 66.7%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

In 30 ml of isopropyl alcohol was dissolved 1 g of 2-nitratoethyl acetoacetate, 1.1 g of 3-nitratopropyl 3-aminocrotonate and 0.79 g of 2-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-acetone=5:2) and recrystallized from ether to obtain 1.11 g of 2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-(2-nitratoethyl) 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-08dbe3d0d0fa45b89035b3c59083c04d
Source dataset
uspto-grants-1984_09
Patent number
US04472411

Reaction notes

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