Oxalyl chloride → 5,6-Dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1,2-dione

HRID 893260Notes

Reaction equation

HRID 893260 reaction equation
[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.[C:11](Cl)(=[O:15])[C:12](Cl)=[O:13]>O1CCCC1>[C:11]1(=[O:15])[C:9]2=[C:10]3[C:5](=[CH:6][CH:7]=[CH:8]2)[CH2:4][CH2:3][CH2:2][N:1]3[C:12]1=[O:13]

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 694601,2,3,4-Tetrahydroquinoline

Product 1

HCID 27861435,6-Dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1,2-dioneYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 1,2,3,4-tetrahydroquinoline (18.5 g) in anhydrous tetrahydrofuran (THF; 150 ml) was added a solution of oxalyl chloride (22 ml) in anhydrous THF (100 ml) dropwise under reflux and reflux was continued for 3.5 hours. After cooling, the reaction mixture was concentrated under reduced pressure. To the resulting residue was added carbon disulfide (800 ml) and refluxed under stirring. To the refluxing mixture was added aluminum chloride (35 g) portionwise during 5 hours, further refluxed for 3 hours and then allowed to stand for overnight. To the reaction mixture, under cooling, was added concentrated hydrochloric acid (150 ml) and then water (150 ml), extracted with chloroform. The organic layer was washed with water, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was recrystallized from ethanol to give the title compound (21 g, 80%) as dark reddish needles, mp 198°-200 ° C.

Workup

  1. temperatureunder reflux
  2. temperaturereflux
  3. temperatureAfter cooling
  4. concentrationthe reaction mixture was concentrated under reduced pressure
  5. additionTo the resulting residue was added carbon disulfide (800 ml)
  6. temperaturerefluxed
  7. additionTo the refluxing mixture was added aluminum chloride (35 g) portionwise during 5 hours
  8. temperaturefurther refluxed for 3 hours
  9. waitto stand for overnight
  10. temperatureTo the reaction mixture, under cooling
  11. additionwas added concentrated hydrochloric acid (150 ml)
  12. extractionwater (150 ml), extracted with chloroform
  13. washThe organic layer was washed with water
  14. dry with materialdried over anhydrous sodium sulfate
  15. concentrationconcentrated under reduced pressure
  16. customThe resulting residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-47b05c4ac9e348869fbfde8a00c95fd9
Source dataset
uspto-grants-1992_06
Patent number
US05124325

Reaction notes

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