Reaction #3248

Reaction equation

3-methyl-5H-indeno[2,1-c]quinoline-6,7-dion

phosphorous oxychloride

→

title compound

Yield 73.4%

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

Yield 73.4%

Conditions

Workup

1. 1
   Temperaturewas refluxed
2. 2
   Temperaturewith heat for 1.5 hours
3. 3
   workup.DISTILLATIONThe reaction mixture was distilled to dryness
4. 4
   workup.ADDITIONTo the residue was added water
5. 5
   Otherto obtain a crystal
6. 6
   Otherprecipitated by filtration
7. 7
   OtherThe crystal obtained
8. 8
   Washwas washed with water
9. 9
   workup.DISSOLUTIONdissolved in chloroform
10. 10
    Filtrationto filter off undissolved substances
11. 11
    OtherRecrystallization from benzene

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.

Source