Phosphorus oxychloride → 2-Chloro-5,6-dihydro-4H-imidazo[1,5,4-de]quinoxaline

HRID 1082053Notes

Reaction equation

HRID 1082053 reaction equation
[NH:1]1[C:11]2[C:12]3[N:3]([CH2:4][CH2:5][NH:6][C:7]=3[CH:8]=[CH:9][CH:10]=2)[C:2]1=O.P(Cl)(Cl)([Cl:16])=O>>[Cl:16][C:2]1[N:3]2[CH2:4][CH2:5][NH:6][C:7]3[CH:8]=[CH:9][CH:10]=[C:11]([C:12]=32)[N:1]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 233620195,6-Dihydro-4H-imidazo[1,5,4-de]quinoxalin-2(1H)-one

Product 1

HCID 233620222-Chloro-5,6-dihydro-4H-imidazo[1,5,4-de]quinoxaline

Procedure

3 g (0.0155 mol) of 5,6-dihydro-4H-imidazo[1,5,4-de]quinoxalin-2(1H)-one in 60 ml of phosphoryl chloride are heated at the reflux temperature for 3 hours. The solvent is evaporated to dryness and the residue taken up successively in ice-cold water and in a concentrated aqueous ammonia solution. Extraction is then carried out twice with ether and the organic phases are combined, dried and evaporated to dryness. The residue is purified by chromatography on a column of silica gel, the eluent being ether. There are obtained 1.8 g of product in the oil form which is used as is in the following stage.

Workup

  1. customThe solvent is evaporated to dryness
  2. extractionExtraction
  3. customdried
  4. customevaporated to dryness
  5. customThe residue is purified by chromatography on a column of silica gel

Sources & evidence

ORD record
ord-b1646ea4ad7749288bd3f60b27d86bd2
Source dataset
uspto-grants-1996_12
Patent number
US05589476

Reaction notes

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