Phosphorus oxychloride → 6-chloro-3-methyl-7H-indeno[2,1-c]quinoline-7-on

HRID 3152Notes

Reaction equation

HRID 3152 reaction equation
[CH3:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]3[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[C:13](=[O:20])[C:7]=3[C:8](=O)[NH:9]2)=[CH:4][CH:3]=1.P(Cl)(Cl)([Cl:23])=O>>[Cl:23][C:8]1[C:7]2[C:13](=[O:20])[C:14]3[C:19]([C:6]=2[C:5]2[C:10](=[CH:11][C:2]([CH3:1])=[CH:3][CH:4]=2)[N:9]=1)=[CH:18][CH:17]=[CH:16][CH:15]=3

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 19356120HCID 19356120, compound

Product 1

HCID 193561186-chloro-3-methyl-7H-indeno[2,1-c]quinoline-7-onYield 73.4%

Procedure

A mixture of 3-methyl-5H-indeno[2,1-c]quinoline-6,7-dion obtained in reference example 5 (700 mg, 2.7 mmol) and phosphorous oxychloride (10 ml, 107 mmol) was refluxed with heat for 1.5 hours. The reaction mixture was distilled to dryness. To the residue was added water to obtain a crystal precipitated by filtration. The crystal obtained was washed with water and dissolved in chloroform to filter off undissolved substances. Recrystallization from benzene to give 550 mg (yield 73.4%) of the title compound.

Workup

  1. temperaturewas refluxed
  2. temperaturewith heat for 1.5 hours
  3. distillationThe reaction mixture was distilled to dryness
  4. additionTo the residue was added water
  5. customto obtain a crystal
  6. customprecipitated by filtration
  7. customThe crystal obtained
  8. washwas washed with water
  9. dissolutiondissolved in chloroform
  10. filtrationto filter off undissolved substances
  11. customRecrystallization from benzene

Sources & evidence

ORD record
ord-d9236b54d4954b7aa9b9f3b9d4ae71c7
Source dataset
uspto-grants-1998_03
Patent number
US05733918

Reaction notes

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