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

HRID 2418255Notes

Reaction equation

HRID 2418255 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 3776IsopropanolSolvent

Procedure

In 70 ml of isopropyl alcohol saturated with ammonia were dissolved 5 g of 2-nitratoethyl acetoacetate and 2 g of 2-nitrobenzaldehyde. The solution was heated at reflux for 5 hours and then treated in the manner described in Example 1 to give 2.51 g of 2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid bis(2-nitratoethyl) ester.

Workup

  1. temperatureThe solution was heated
  2. temperatureat reflux for 5 hours
  3. additiontreated in the manner

Sources & evidence

ORD record
ord-ada7f66512794fe196afbf17aa076bfa
Source dataset
uspto-grants-1984_09
Patent number
US04472411

Reaction notes

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