Oxalyl chloride → Methyl 5,6-dihydro-1,2-dioxo-4H-pyrrolo[3,2,1-ij]quinoline-6-carboxylate

HRID 1195744Notes

Reaction equation

HRID 1195744 reaction equation
[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]([C:11]([O:13][CH3:14])=[O:12])[CH2:3][CH2:2]1.[C:15](Cl)(=[O:19])[C:16](Cl)=[O:17]>O1CCCC1>[O:17]=[C:16]1[C:9]2=[C:10]3[C:5](=[CH:6][CH:7]=[CH:8]2)[CH:4]([C:11]([O:13][CH3:14])=[O:12])[CH2:3][CH2:2][N:1]3[C:15]1=[O:19]

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 10631570Methyl 1,2,3,4-tetrahydroquinoline-4-carboxylate

Product 1

HCID 15157734Methyl 5,6-dihydro-1,2-dioxo-4H-pyrrolo[3,2,1-ij]quinoline-6-carboxylateYield 83.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of methyl 1,2,3,4-tetrahydroquinoline-4-carboxylate (51.0 g) in tetrahydrofuran (THF, 200 ml) was heated under refluxing and a solution of oxalyl chloride (30 ml) in dry THF was added thereto. The mixture was refluxed for 4 hours, then cooled and concentrated. The residue was dissolved in carbon disulfide (800 ml) and aluminum chloride (66.7 g) was added portionwise. The mixture was refluxed for 4 hours, and then allowed to stand overnight. The solvent was eliminated by decantation and to the residue was added ice-water (1 litter). The mixture was extracted with chloroform. The chloroform layer was washed well with water, dried over anhydrous sodium sulfate and concentrated to give the title compound (55.15 g, 83.3%) which was recrystallized from acetonitrile to dark red crystals, mp 135° C.-136° C.

Workup

  1. temperatureunder refluxing
  2. temperatureThe mixture was refluxed for 4 hours
  3. temperaturecooled
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved in carbon disulfide (800 ml)
  6. additionaluminum chloride (66.7 g) was added portionwise
  7. temperatureThe mixture was refluxed for 4 hours
  8. additionwas added ice-water (1 litter)
  9. extractionThe mixture was extracted with chloroform
  10. washThe chloroform layer was washed well with water
  11. dry with materialdried over anhydrous sodium sulfate
  12. concentrationconcentrated

Sources & evidence

ORD record
ord-ebe9810d28cb40f98bbd0b23c3e202e5
Source dataset
uspto-grants-1992_05
Patent number
US05112836

Reaction notes

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