Phosphorus oxychloride → 2-Pyridone

HRID 1385954Notes

Reaction equation

HRID 1385954 reaction equation
ClC1C=CC([CH:8]2[C:13](=[O:14])[CH:12]=[C:11](C(F)(F)F)[N:10](C)[C:9]2=[O:20])=CC=1.P(Cl)(Cl)(Cl)=O>CCN(C1C=CC=CC=1)CC>[NH:10]1[CH:11]=[CH:12][CH:13]=[CH:8][C:9]1=[O:20].[N:10]1[CH:9]=[CH:8][C:13](=[O:14])[CH2:12][CH:11]=1

Participants

5

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 184083273-(4-Chlorophenyl)-2,4-dioxo-1-methyl-6-trifluoromethyl-1,2,3,4-tetrahydropyridine

Product 2

HCID 88712-PyridoneYield 37%HCID 17984897Piridin-4-oneYield 29%

Reagents, catalysts & solvents 1

HCID 7061N,N-DiethylanilineSolvent

Conditions

Temperature
110 °C

Procedure

3.3 g (10.9 mmol) of 3-(4-chlorophenyl)-2,4-dioxo-1-methyl-6-trifluoromethyl-1,2,3,4-tetrahydropyridine was added to 8.3 g (42.3 mmol) of phosphorus oxychloride and 30 ml of diethylaniline, followed by stirring at from 100 to 120° C. for 4 hours. The reaction solution was distilled off under reduced pressure, and ethyl acetate was added to the obtained residue, followed by washing with water and a saturated sodium hydrogencarbonate aqueous solution. The organic layer was dried over anhydrous magnesium sulfate. The organic layer was distilled off under reduced pressure, and the obtained residue was separated and purified by high performance liquid chromatography to obtain 1.3 g (yield: 37%) of the desired 2-pyridone compound (Compound No. 11-1) and 1.0 g (yield: 29%) of the 4-pyridone compound (Compound No. 13-1), respectively.

Workup

  1. distillationThe reaction solution was distilled off under reduced pressure, and ethyl acetate
  2. additionwas added to the obtained residue
  3. washby washing with water
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. distillationThe organic layer was distilled off under reduced pressure
  6. customthe obtained residue was separated
  7. custompurified by high performance liquid chromatography

Sources & evidence

ORD record
ord-dbf87c2a269d422c905fd4c84321c377
Source dataset
uspto-grants-2001_07
Patent number
US06265349B1

Reaction notes

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