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

HRID 1198465Notes

Reaction equation

HRID 1198465 reaction equation
[C:1](Cl)(=[O:5])[C:2](Cl)=[O:3].[NH:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10][CH2:9][CH2:8]1>O1CCCC1>[C:1]1(=[O:5])[C:15]2=[C:16]3[C:11](=[CH:12][CH:13]=[CH:14]2)[CH2:10][CH2:9][CH2:8][N:7]3[C:2]1=[O:3]

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-dione

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To the refluxing mixture of oxalyl chloride (22 ml) in dry tetrahydrofuran (THF, 100 ml) was added 1,2,3,4-tetrahydroquinoline (18.5 g) in dry THF (150 ml) dropwise. The mixture was refluxed for 3.5 hours after addition was completed, then cooled to room temperature and concentrated under reduced pressure. The residue was dissolved in carbon disulfide (800 ml) and heated up to reflux. To the refluxing mixture was added aluminum chloride (35 g) portionwise over 5 hours period under stirring. The reaction mixture was refluxed for an additional 3 hours and allowed to stand for overnight at room temperature. After decantation of the solvent, the residue, cooled by an ice bath, was treated with water (150 ml). The mixture was extracted with chloroform and washed with water and dried over anhydrous sodium sulfate. Evaporation of chloroform afforded the title compound The compound was recrystallized from ethanol to give 21 g (80%) of dark red needles, mp 198°-200° C.

Workup

  1. temperatureThe mixture was refluxed for 3.5 hours
  2. additionafter addition
  3. concentrationconcentrated under reduced pressure
  4. dissolutionThe residue was dissolved in carbon disulfide (800 ml)
  5. temperatureheated up
  6. temperatureto reflux
  7. additionTo the refluxing mixture was added aluminum chloride (35 g) portionwise over 5 hours period
  8. temperatureThe reaction mixture was refluxed for an additional 3 hours
  9. temperatureAfter decantation of the solvent, the residue, cooled by an ice bath
  10. additionwas treated with water (150 ml)
  11. extractionThe mixture was extracted with chloroform
  12. washwashed with water
  13. dry with materialdried over anhydrous sodium sulfate
  14. customEvaporation of chloroform

Sources & evidence

ORD record
ord-7383b06f6b544853826b0dcb9f75d759
Source dataset
uspto-grants-1994_01
Patent number
US05281600

Reaction notes

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