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

HRID 1789996Notes

Reaction equation

HRID 1789996 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-fbaa14d6e4c243d89586713fa1c24c59
Source dataset
uspto-grants-2006_07
Patent number
US07071192B1

Reaction notes

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