N,N-Dimethylaniline → 2-Chloroquinoxaline

HRID 616871Notes

Reaction equation

HRID 616871 reaction equation
O[C:2]1[CH:3]=[N:4][C:5]2[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=2[N:7]=1.CN(C)C1C=CC=CC=1.P(Cl)(Cl)([Cl:23])=O>>[Cl:23][C:2]1[CH:3]=[N:4][C:5]2[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=2[N:7]=1

Participants

4

Reactant 3

HCID 949N,N-DimethylanilineHCID 24813Phosphorus oxychlorideHCID 178516710HCID 178516710, compound

Product 1

HCID 2389382-ChloroquinoxalineYield 87.5%

Procedure

A mixture of 74 g (0.5 mole) of 2-hydroxy-benzopyrazine, 12 g of dimethylaniline and 250 ml of phosphorus oxychloride was heated under reflux for 10 minutes. At about 80° C, all the material had dissolved; the reaction solution was cooled and poured onto ice, and the product was filtered off. The residue was dried on clay and was then taken up in petroleum ether, and the solution was filtered through active charcoal. The reaction solution was evaporated and 78 g (87.5% of theory) of 2-chloro-benzopyrazine of melting point 48°-49° C, were obtained. ##STR33##

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 10 minutes
  3. dissolutionAt about 80° C, all the material had dissolved
  4. temperaturethe reaction solution was cooled
  5. additionpoured onto ice
  6. filtrationthe product was filtered off
  7. customThe residue was dried on clay
  8. filtrationthe solution was filtered through active charcoal
  9. customThe reaction solution was evaporated

Sources & evidence

ORD record
ord-40a644e6f6834759b60dd39293b5ff55
Source dataset
uspto-grants-1978_02
Patent number
US04076806

Reaction notes

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