Phosphorus oxychloride → 5-chloro-7H-indeno[2,1-c]isoquinoline-7-on

HRID 3154Notes

Reaction equation

HRID 3154 reaction equation
[CH:1]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:2]=1[C:3]1[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12](=[O:19])[C:4]=1[NH:5][C:6]2=O.P(Cl)(Cl)([Cl:22])=O>CN(C)C=O>[Cl:22][C:6]1[C:7]2[C:2](=[CH:1][CH:10]=[CH:9][CH:8]=2)[C:3]2[C:18]3[C:13]([C:12](=[O:19])[C:4]=2[N:5]=1)=[CH:14][CH:15]=[CH:16][CH:17]=3

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 193561396H-indeno[2,1-c]isoquinoline-5,7-dion

Product 1

HCID 193561405-chloro-7H-indeno[2,1-c]isoquinoline-7-onYield 78.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 6H-indeno[2,1-c]isoquinoline-5,7-dion obtained in reference example 16 (26.6 g, 108 mmol) and phosphorous oxychloride (300 ml) was refluxed with heat in the presence of 1 ml of N,N-dimethylformamide for 2 hours. The reaction mixture was distilled to dryness. To the residue was added ice water to obtain a crystal precipitated by filtration. The crystal obtained was washed with water and recrystallized from toluene to give 22.5 g (yield 78.7%) of the title compound.

Workup

  1. temperaturewas refluxed
  2. distillationThe reaction mixture was distilled to dryness
  3. additionTo the residue was added ice water
  4. customto obtain a crystal
  5. customprecipitated by filtration
  6. customThe crystal obtained
  7. washwas washed with water
  8. customrecrystallized from toluene

Sources & evidence

ORD record
ord-bd6b84b0847d406aae39ab734c84c1c7
Source dataset
uspto-grants-1998_03
Patent number
US05733918

Reaction notes

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