Ethyl Acetate → HCID 14988431, compound

HRID 1198468Notes

Reaction equation

HRID 1198468 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].[Br:15]N1C(=O)CCC1=O.C(OCC)(=O)C>CN(C=O)C>[Br: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

5

Reactant 3

HCID 8857Ethyl AcetateHCID 67184N-bromobutanimideHCID 27861435,6-Dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1,2-dione

Product 1

HCID 14988431HCID 14988431, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1,2-dione (10 g) and N-bromosuccinimide (10 g) in DMF (60 ml) was stirred at 7020 C. for 5 hours. After cooling, to the mixture was added ethyl acetate (500 ml) and washed with water and saturated aqueous sodium chloride solution successively, and then dried over anhydrous sodium sulfate. Evaporation of ethyl acetate afforded the title compound. The compound was recrystallized from ethanol to give 14 g (98.4%) as dark red needles.

Workup

  1. temperatureAfter cooling, to the mixture
  2. washwashed with water and saturated aqueous sodium chloride solution successively
  3. dry with materialdried over anhydrous sodium sulfate
  4. customEvaporation of ethyl acetate

Sources & evidence

ORD record
ord-6d3b7d39f6ed4ef99500f80b90776203
Source dataset
uspto-grants-1994_01
Patent number
US05281600

Reaction notes

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