Chlorosuccinimide → HCID 13575826, compound

HRID 1981568Notes

Reaction equation

HRID 1981568 reaction equation
[C:1]1(=[O:14])[C:11]2=[C:12]3[C:7](=[CH:8][CH:9]=[CH:10]2)[CH2:6][CH2:5][CH2:4][N:3]3[C:2]1=[O:13].[Cl:15]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Cl:15][C:9]1[CH:8]=[C:7]2[C:12]3=[C:11]([C:1](=[O:14])[C:2](=[O:13])[N:3]3[CH2:4][CH2:5][CH2:6]2)[CH:10]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 27861435,6-Dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1,2-dione

Product 1

HCID 13575826HCID 13575826, compoundYield 47.4%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1,2-dione (7.49 g, 0.04 mole) and N-chlorosuccinimide (5.34 g, 0.04 mole) in carbon tetrachloride (40 ml) was refluxed for 23 hours. After cooling, the resultant red precipitate was collected by filteration, washed with water and dried. Recrystallization from acetonitrile afforded 4.2 g (47.4%) of red needles, melted at 188°-189° C.

Workup

  1. temperaturewas refluxed for 23 hours
  2. temperatureAfter cooling
  3. customthe resultant red precipitate was collected by filteration
  4. washwashed with water
  5. customdried
  6. customRecrystallization from acetonitrile

Sources & evidence

ORD record
ord-6c4b9525bd1f46bfb8b54e8061cf280f
Source dataset
uspto-grants-1986_06
Patent number
US04593092

Reaction notes

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