Phosphorus oxychloride → 2-Chloro-4-(2-chloro-4-difluoromethoxy-phenyl)-3-nitro-2,3-dihydro-pyridine

HRID 1831550Notes

Reaction equation

HRID 1831550 reaction equation
O=P(Cl)(Cl)[Cl:3].[Cl:6][C:7]1[CH:12]=[C:11]([O:13][CH:14]([F:16])[F:15])[CH:10]=[CH:9][C:8]=1[C:17]1[CH:18]([N+:24]([O-:26])=[O:25])[C:19](=O)[N:20]=[CH:21][CH:22]=1>CN(C=O)C>[Cl:3][CH:19]1[CH:18]([N+:24]([O-:26])=[O:25])[C:17]([C:8]2[CH:9]=[CH:10][C:11]([O:13][CH:14]([F:16])[F:15])=[CH:12][C:7]=2[Cl:6])=[CH:22][CH:21]=[N:20]1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 220521384-(2-chloro-4-difluoromethoxy-phenyl)3-nitro-3H-pyridin-2-one

Product 1

HCID 220520842-Chloro-4-(2-chloro-4-difluoromethoxy-phenyl)-3-nitro-2,3-dihydro-pyridineYield 96%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 10 mL of POCl3 was added 4-(2-chloro-4-difluoromethoxy-phenyl)3-nitro-3H-pyridin-2-one (0.20 g, 0.63 mmol), followed by the addition of DMF (1–2 mL) and the reaction refluxed overnight. The reaction mixture was cooled to room temperature and poured over ice/H2O (200 mL). The solution was extracted with EtOAc, washed H2O, brine, dried Na2SO4, filtered, and concentrated in vacuo to give 0.176 g (96%) of 2-chloro-4-(2-chloro-4-difluoromethoxy-phenyl)-3-nitro-2,3-dihydro-pyridine as brown viscous oil.

Workup

  1. temperaturethe reaction refluxed overnight
  2. extractionThe solution was extracted with EtOAc
  3. washwashed H2O, brine, dried Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e2e66cbba6904a6cbefe7273563f8970
Source dataset
uspto-grants-2006_06
Patent number
US07067658B2

Reaction notes

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