3-Nitro-2-phenyl-pyridine-1-oxide → HCID 71757322, compound

HRID 508483Notes

Reaction equation

HRID 508483 reaction equation
[N+:1]([C:4]1[C:5]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N+:6]([O-])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[Cl-:17].[P+]=O>ClCCCl>[Cl:17][C:7]1[N:6]=[C:5]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 669400123-Nitro-2-phenyl-pyridine-1-oxideHCID 178527006HCID 178527006, compound

Product 1

HCID 71757322HCID 71757322, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

In a 100 ml single-necked round-bottomed flask equipped with a condensor, 5.00 g of 3-nitro-2-phenyl-pyridine-1-oxide is dissolved in 25.0 ml dry 1,2-dichloroethane. Phosphorous oxide chloride (3.18 ml) is added carefully (yellow-orange solution). This mixture is then stirred under heating to reflux for 17 h. After cooling the mixture to ambient temperature. Ice/water is added then. The extraction is carried out with dichloromethane (2×50 ml). After washing with brine, the organic phase is dried over sodium sulfate, filtered and concentrated in vacuo. Purification by flash chromatography over a silica gel cartridge (25 g, 150 ml) of a solid deposition with hexane/ethyl acetate 4:1 (v:v) gives 2.61 g of the title compound as a yellow oil.

Workup

  1. temperatureunder heating
  2. temperatureto reflux for 17 h
  3. extractionThe extraction
  4. washAfter washing with brine
  5. dry with materialthe organic phase is dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customPurification by flash chromatography over a silica gel cartridge (25 g, 150 ml) of a solid deposition with hexane/ethyl acetate 4:1 (v:v)

Sources & evidence

ORD record
ord-6acebf2b881a47ac9f9cb395ec1acdde
Source dataset
uspto-grants-2015_08
Patent number
US09096525B2

Reaction notes

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