Nitric Acid → 3,4-Diethoxycarbonyl-6-(4-methoxyphenyl)-5-nitro-2(1H)pyridone

HRID 37482Notes

Reaction equation

HRID 37482 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:25])[NH:8][C:9]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)=[CH:10][C:11]=1[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[O:5])[CH3:2].[N+:26]([O-])([OH:28])=[O:27].O>C(OC(=O)C)(=O)C>[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:25])[NH:8][C:9]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)=[C:10]([N+:26]([O-:28])=[O:27])[C:11]=1[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 962WaterHCID 199355943,4-Diethoxycarbonyl-6-(4-methoxyphenyl)-2-pyridone

Product 1

HCID 199356143,4-Diethoxycarbonyl-6-(4-methoxyphenyl)-5-nitro-2(1H)pyridone

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
-30 °C

Procedure

In 8 ml of acetic anhydride was suspended 1.2 g of 3,4-diethoxycarbonyl-6-(4-methoxyphenyl)-2(1H)pyridone. After the mixture was cooled to -30° C. 0 36 ml of fuming nitric acid was added dropwise, followed by stirring for 45 minutes. After water was added, stirring was continued for further 1 hour. The viscous product was collected by filtration, crystallized with diethyl ether and washed.

Workup

  1. stirringstirring
  2. waitwas continued for further 1 hour
  3. filtrationThe viscous product was collected by filtration
  4. customcrystallized with diethyl ether
  5. washwashed

Sources & evidence

ORD record
ord-15d31b3435d449ba88e4a5b2d8d62c85
Source dataset
uspto-grants-1995_05
Patent number
US05420275

Reaction notes

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