Phosphorus oxychloride → 1-Benzyl-4-chloro-3-nitropyridin-2(1H)-one

HRID 2244797Notes

Reaction equation

HRID 2244797 reaction equation
[CH2:1]([N:8]1[CH:13]=[CH:12][C:11](O)=[C:10]([N+:15]([O-:17])=[O:16])[C:9]1=[O:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O=P(Cl)(Cl)[Cl:21]>>[CH2:1]([N:8]1[CH:13]=[CH:12][C:11]([Cl:21])=[C:10]([N+:15]([O-:17])=[O:16])[C:9]1=[O:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 587884461-Benzyl-4-hydroxy-3-nitropyridin-2(1H)-one

Product 1

HCID 249444631-Benzyl-4-chloro-3-nitropyridin-2(1H)-oneYield 37%

Procedure

A suspension of 1-benzyl-4-hydroxy-3-nitro-1H-pyridine-2-one (3.30 g, 13.4 mmol) in POCl3 (30.8 g, 201 mmol) was heated at for 1 h. After cooling to room temperature, the solvent was evaporated under reduced pressure, and water was carefully added to the chilled residue. The mixture was neutralized with 2 N NaOH, extracted with CHCl3, washed with brine, dried with MgSO4, and concentrated under reduced pressure. The resulting solid was rinsed with Et2O to give 1-benzyl-4-chloro-3-nitro-1H-pyridin-2-one (1.31 g, 37% yield). 1H-NMR (CDCl3): δ 7.36 (m, 6H), 6.29 (d, 1H, J=7.6 Hz), 5.16 (s, 2H). MS: calculated for C12H9ClN2O3+H 265.0; found: 265.1.

Workup

  1. temperaturewas heated at for 1 h
  2. customthe solvent was evaporated under reduced pressure, and water
  3. additionwas carefully added to the chilled residue
  4. extractionextracted with CHCl3
  5. washwashed with brine
  6. dry with materialdried with MgSO4
  7. concentrationconcentrated under reduced pressure
  8. washThe resulting solid was rinsed with Et2O

Sources & evidence

ORD record
ord-513114acebed45a0b95370922b50b640
Source dataset
uspto-grants-2010_03
Patent number
US07678909B1

Reaction notes

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