Chlorosuccinimide → HCID 19892016, compound

HRID 893261Notes

Reaction equation

HRID 893261 reaction equation
[C:1]1([CH:7]2[CH2:16][CH2:15][C:14]3[C:9]4=[C:10]([C:17](=[O:20])[C:18](=[O:19])[N:8]24)[CH:11]=[CH:12][CH:13]=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:21]N1C(=O)CCC1=O>CN(C)C=O>[Cl:21][C:12]1[CH:13]=[C:14]2[C:9]3=[C:10]([C:17](=[O:20])[C:18](=[O:19])[N:8]3[CH:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH2:16][CH2:15]2)[CH:11]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 14988427HCID 14988427, compound

Product 1

HCID 19892016HCID 19892016, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 5,6-dihydro-4-phenyl-4H-pyrrolo[3,2,1-ij]-quinoline-1,2-dione (3.1 g) and N-chlorosuccinimide (1.89 g) in dimethylformamide (DMF; 50 ml) was stirred at 80 ° C. for an hour. After cooling, the mixture was concentrated under reduced pressure and to the resulting residue was added chloroform (500 ml). The organic layer was washed with water and saturated aqueous sodium chloride solution, dried over sodium sulfate and concentrated under reduced pressure to give the title compound (3.4 g, 96.8%). This crystals was recrystallized from acetonitrile to give dark reddish crystals, mp 173°-174 ° C.

Workup

  1. temperatureAfter cooling
  2. concentrationthe mixture was concentrated under reduced pressure and to the resulting residue
  3. additionwas added chloroform (500 ml)
  4. washThe organic layer was washed with water and saturated aqueous sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-98f45929e1514f92aac225c621720518
Source dataset
uspto-grants-1992_06
Patent number
US05124325

Reaction notes

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