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

HRID 2418256Notes

Reaction equation

HRID 2418256 reaction equation
[C:1]([O-:7])(=[O:6])[CH2:2][C:3]([CH3:5])=O.[N+:8]([C:11]1[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=1[CH:13]=O)([O-:10])=[O:9].[NH3:19]>C(O)(C)C>[CH3:5][C:3]1[NH:19][C:3]([CH3:5])=[C:2]([C:1]([OH:7])=[O:6])[CH:13]([C:12]2[CH:15]=[CH:16][CH:17]=[CH:18][C:11]=2[N+:8]([O-:10])=[O:9])[C:2]=1[C:1]([OH:7])=[O:6]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 111012-NitrobenzaldehydeHCID 6971017Acetoacetate

Product 1

HCID 120733112,6-Dimethyl-3,5-dicarboxy-4-(2-nitrophenyl)-1,4-dihydropyridine

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Procedure

In 30 ml of isopropyl alcohol were dissolved 2 g of 3-nitratopropyl acetoacetate and 0.74 g of 2-nitrobenzaldehyde. To the solution was added 4 ml of isopropyl alcohol saturated with an ammonia gas at 10° C. The mixture 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=5:3) and recrystallized from ether to obtain 1.11 g of 2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid bis(3-nitratopropyl) ester.

Workup

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

Sources & evidence

ORD record
ord-d0dbdb950b934b149ce1c59523593e5f
Source dataset
uspto-grants-1984_09
Patent number
US04472411

Reaction notes

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