Water → Y 9000

HRID 1579387Notes

Reaction equation

HRID 1579387 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5]([C:8]1[CH:23]=[CH:22][C:11]([O:12][C:13]2[N:21]=[CH:20][CH:19]=[CH:18][C:14]=2[C:15](Cl)=[O:16])=[CH:10][CH:9]=1)(=[O:7])[CH3:6].O>[N+](C1C=CC=CC=1)([O-])=O>[C:5]([C:8]1[CH:23]=[CH:22][C:11]2[O:12][C:13]3=[N:21][CH:20]=[CH:19][CH:18]=[C:14]3[C:15](=[O:16])[C:10]=2[CH:9]=1)(=[O:7])[CH3:6]

Participants

5

Reactant 3

HCID 962WaterHCID 6451240Aluminum(III) Chloride2×HCID 21568411HCID 21568411, compound

Product 1

HCID 198324Y 9000

Reagents, catalysts & solvents 1

HCID 7416NitrobenzeneSolvent

Conditions

Temperature
80 °C

Procedure

1.68 g of powdered anhydrous aluminum chloride is added to a solution of 1.15 g of 2-(p-acetylphenoxy)nicotinoyl chloride in 5 ml of nitrobenzene at 20°-30°C, and the mixture is heated at 80°C for 3.5 hours. After cooling, water is added to the reaction mixture to decompose the aluminum chloride. After removing the nitrobenzene by distillation, the mixture is extracted with chloroform, and the extract is concentrated. The residue is recrystallized from toluene to give 7-acetyl-5-oxo-5H-[1]benzopyrano[2,3-b]pyridine melting at 195-196°C.

Workup

  1. temperatureAfter cooling
  2. customAfter removing the nitrobenzene
  3. distillationby distillation
  4. extractionthe mixture is extracted with chloroform
  5. concentrationthe extract is concentrated
  6. customThe residue is recrystallized from toluene

Sources & evidence

ORD record
ord-20b137777e704d1aabeeb6b3344aa5ba
Source dataset
uspto-grants-1976_01
Patent number
US03931199

Reaction notes

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