Ethyl Acetate → HCID 14988431, compound

HRID 1031914Notes

Reaction equation

HRID 1031914 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

Conditions

Temperature
70 °C

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 70° 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-e4515dcdab0246568436c877a7084409
Source dataset
uspto-grants-1990_09
Patent number
US04956372

Reaction notes

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