Phosphorus oxychloride → 2-Chloro-6,7-difluoro-3-methylquinoxaline

HRID 584659Notes

Reaction equation

HRID 584659 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[F:12])[NH:8][C:7](=O)[C:6]([CH3:14])=[N:5]2.O=P(Cl)(Cl)[Cl:17]>CN(C)C1C=CN=CC=1>[Cl:17][C:7]1[C:6]([CH3:14])=[N:5][C:4]2[C:9](=[CH:10][C:11]([F:12])=[C:2]([F:1])[CH:3]=2)[N:8]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 3894396,7-difluoro-3-methyl-1H-quinoxalin-2-one

Product 1

HCID 102200112-Chloro-6,7-difluoro-3-methylquinoxaline

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

6,7-Difluoro-3-methyl-1H-quinoxalin-2-one (2 g, prepared from 4,5-difluoro-1,2-phenylene-diamine and pyruvic acid according to general procedure (A), step 1) was mixed with POCl3 (20 ml) and 4-dimethylaminopyridine (10 mol %) and the mixture was refluxed for 2 hours. The mixture was allowed to cool and poured onto ice (300 ml), filtered and washed with water to afford the title compound.

Workup

  1. temperaturethe mixture was refluxed for 2 hours
  2. temperatureto cool
  3. additionpoured onto ice (300 ml)
  4. filtrationfiltered
  5. washwashed with water

Sources & evidence

ORD record
ord-9e777484c7d441c3b6d1d48e99f1e23d
Source dataset
uspto-grants-2005_08
Patent number
US06927214B1

Reaction notes

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