Nitric Acid → Y 9000

HRID 1579400Notes

Reaction equation

HRID 1579400 reaction equation
[N+]([O-])(O)=O.[Mn]([O-])(=O)(=O)=O.[K+].[O-2:11].[Mg+2].[CH2:13]([C:15]1[CH:16]=[CH:17][C:18]2[O:27][C:22]3=[N:23][CH:24]=[CH:25][CH:26]=[C:21]3[C:20](=[O:28])[C:19]=2[CH:29]=1)[CH3:14]>O>[C:13]([C:15]1[CH:16]=[CH:17][C:18]2[O:27][C:22]3=[N:23][CH:24]=[CH:25][CH:26]=[C:21]3[C:20](=[O:28])[C:19]=2[CH:29]=1)(=[O:11])[CH3:14]

Participants

6

Reactant 4

HCID 944Nitric AcidHCID 516875Potassium PermanganateHCID 6850729Magnesium monoxideHCID 12689276HCID 12689276, compound

Product 1

HCID 198324Y 9000Yield 67%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

7.6 ml of nitric acid (specific gravity 1.38) and 7.9 g of potassium permanganate are added to a suspension of 2 g of magnesium oxide in 50 ml of water, and the mixture is heated to 60°C. To the mixture is added 4.5 g of 7-ethyl-5-oxo-5H-[1]benzopyrano[2,3-b]pyridine over a period of 30 minutes with stirring, keeping the temperature at 60°-70°C. After the addition the mixture is stirred at 60°-70°C for 4.5 hours. After cooling, the reaction mixture is filtered under reduced pressure, and the residue containing manganese dioxide is extracted several times with chloroform. The chloroform layer is washed with water, dried, and the chloroform is distilled off. The residue is recrystallized from toluene to give 3.2 g of 7-acetyl-5-oxo-5H-[1]benzopyrano[2,3-b]pyridine melting at 195°-196°C.

Workup

  1. customat 60°-70°C
  2. additionAfter the addition the mixture
  3. stirringis stirred at 60°-70°C for 4.5 hours
  4. temperatureAfter cooling
  5. filtrationthe reaction mixture is filtered under reduced pressure
  6. additionthe residue containing manganese dioxide
  7. extractionis extracted several times with chloroform
  8. washThe chloroform layer is washed with water
  9. customdried
  10. distillationthe chloroform is distilled off
  11. customThe residue is recrystallized from toluene

Sources & evidence

ORD record
ord-89d1f736538b45978b4be8a93a2bd148
Source dataset
uspto-grants-1976_01
Patent number
US03931199

Reaction notes

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