Chlorosuccinimide → Methyl 8-chloro-5,6-dihydro-1,2-dioxo-4H-pyrrolo[3,2,1-ij]-quinoline-6-carboxylate

HRID 1195745Notes

Reaction equation

HRID 1195745 reaction equation
[O:1]=[C:2]1[C:12]2=[C:13]3[C:8](=[CH:9][CH:10]=[CH:11]2)[CH:7]([C:14]([O:16][CH3:17])=[O:15])[CH2:6][CH2:5][N:4]3[C:3]1=[O:18].C1C(=O)N([Cl:26])C(=O)C1>CN(C)C=O>[Cl:26][C:10]1[CH:9]=[C:8]2[C:13]3=[C:12]([C:2](=[O:1])[C:3](=[O:18])[N:4]3[CH2:5][CH2:6][CH:7]2[C:14]([O:16][CH3:17])=[O:15])[CH:11]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 15157734Methyl 5,6-dihydro-1,2-dioxo-4H-pyrrolo[3,2,1-ij]quinoline-6-carboxylate

Product 1

HCID 15157736Methyl 8-chloro-5,6-dihydro-1,2-dioxo-4H-pyrrolo[3,2,1-ij]-quinoline-6-carboxylateYield 96.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of methyl 5,6-dihydro-1,2-dioxo-4H-pyrrolo[3,2,1-ij]quinoline-6-carboxylate (Example 1; 3 g)and N-cholorsuccinimide (NCS, 1.96 g) in dimethylformamide (DMF, 30 ml) was heated at 80° C. with stirring for an hour. After cooling, the mixture was concentrated. The residue was extracted with chloroform (200 ml). Chloroform layer was washed with water, dried over anhydrous sodium sulfate and concentrated to give the title compound (3.28 g, 96.2%) which was recrystallized form acetonitrile to dark red needles, mp 132° C.-133° C.

Workup

  1. temperatureAfter cooling
  2. concentrationthe mixture was concentrated
  3. extractionThe residue was extracted with chloroform (200 ml)
  4. washChloroform layer was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c6b74f499250489f8ca6aba139ee51cd
Source dataset
uspto-grants-1992_05
Patent number
US05112836

Reaction notes

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