Phosphorus oxychloride → 2-Chloro-4-(2,4-dichloro-phenyl)-3-nitro-pyridine

HRID 1831506Notes

Reaction equation

HRID 1831506 reaction equation
O=P(Cl)(Cl)[Cl:3].[Cl:6][C:7]1[CH:12]=[C:11]([Cl:13])[CH:10]=[CH:9][C:8]=1[C:14]1[CH:19]=[CH:18][NH:17][C:16](=O)[C:15]=1[N+:21]([O-:23])=[O:22]>CN(C=O)C>[Cl:3][C:16]1[C:15]([N+:21]([O-:23])=[O:22])=[C:14]([C:8]2[CH:9]=[CH:10][C:11]([Cl:13])=[CH:12][C:7]=2[Cl:6])[CH:19]=[CH:18][N:17]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 220520964-(2,4-dichloro-phenyl)-3-nitro-1H-pyridin-2-one

Product 1

HCID 220521022-Chloro-4-(2,4-dichloro-phenyl)-3-nitro-pyridineYield 19%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 10 mL of POCl3 was added 4-(2,4-dichloro-phenyl)-3-nitro-1H-pyridin-2-one (1.0 g, 3.51 mmol), followed by the addition of DMF (1-2 mL) and the reaction refluxed for 5 h. The reaction mixture was cooled to room temperature and poured over ice-H2O (200 mL). The solution was extracted with EtOAc, washed with H2O, brine, dried (MgSO4), filtered, and concentrated in vacuo to give 0.20 g (19%) of 2-chloro-4-(2,4-dichloro-phenyl)-3-nitro-pyridine as a brown viscous oil: crude 1H NMR (300 MHz, CDCl3): δ 8.6 (d, 1H), 7.5 (s, 1H), 7.38 (s, 1H), 7.34 (d, 1H), 7.20 (d, 1H).

Workup

  1. temperaturethe reaction refluxed for 5 h
  2. extractionThe solution was extracted with EtOAc
  3. washwashed with H2O, brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d214a31713bd465fafc8bed2abe493b5
Source dataset
uspto-grants-2006_06
Patent number
US07067658B2

Reaction notes

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