Nitric Acid → Diethyl 2-hydroxy-5-nitro-6-phenylpyridine-3,4-dicarboxylate

HRID 37467Notes

Reaction equation

HRID 37467 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:23])[NH:8][C:9]([C:17]2[CH:22]=[CH:21][CH:20]=[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+:24]([O-])([OH:26])=[O:25].O>C(OC(=O)C)(=O)C>[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:23])[NH:8][C:9]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[C:10]([N+:24]([O-:26])=[O:25])[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 199356223,4-Diethyl 1,2-dihydro-2-oxo-6-phenyl-3,4-pyridinedicarboxylate

Product 1

HCID 19935597Diethyl 2-hydroxy-5-nitro-6-phenylpyridine-3,4-dicarboxylate

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
-10 °C

Procedure

In 13 ml of acetic anhydride was suspended 5.0 g of 3,4-diethoxycarbonyl-6-phenyl-2-pyridone; and the suspension was cooled to -10° C. Fuming nitric acid (1.32 ml; 2.0 eq.) was added dropwise over 1 hour, and the mixture was stirred for 45 minutes as it is. After 40 ml of water was added, the mixture was stirred at room temperature and left standing overnight. The resulting crystals were collected by filtration and dried. Yield: 4.61 g (80.7%). The crystals were recrystallized from ethanol, to give pale yellow needles.

Workup

  1. stirringthe mixture was stirred at room temperature
  2. waitleft
  3. waitstanding overnight
  4. filtrationThe resulting crystals were collected by filtration
  5. customdried
  6. customThe crystals were recrystallized from ethanol
  7. customto give pale yellow needles

Sources & evidence

ORD record
ord-e342f0c7d68b44bd8e2ea2fdc7010758
Source dataset
uspto-grants-1995_05
Patent number
US05420275

Reaction notes

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