Phosphorus oxychloride → 2-Chloro-5,6,7,8-tetrahydroquinoxaline

HRID 2217296Notes

Reaction equation

HRID 2217296 reaction equation
[NH:1]1[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[N:4]=[CH:3][C:2]1=O.P(Cl)(Cl)([Cl:14])=O>>[Cl:14][C:2]1[CH:3]=[N:4][C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:10]=2[N:1]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 8202241,2,5,6,7,8-Hexahydroquinoxalin-2-one

Product 1

HCID 220369342-Chloro-5,6,7,8-tetrahydroquinoxalineYield 86%

Procedure

A mixture of 5,6,7,8-tetrahydro-2(1H)-quinoxalinone in phosphoryl chloride (200 ml) was stirred and refluxed for 3 hours. The solvent was evaporated. The residue was taken up in ice and CH2Cl2. The mixture was basified with NH4OH. The organic layer was separated, dried (MgSO4), filtered and the solvent was evaporated, yielding 34 g (86%) of 2-chloro-5,6,7,8-tetrahydroquinoxaline (interm. 3).

Workup

  1. temperaturerefluxed for 3 hours
  2. customThe solvent was evaporated
  3. customThe organic layer was separated
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent was evaporated

Sources & evidence

ORD record
ord-397cd1b96a6b4be38fc7ecd96ca7ec07
Source dataset
uspto-grants-2008_08
Patent number
US07407969B2

Reaction notes

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