Iodine chloride → HCID 14988432, compound

HRID 1031915Notes

Reaction equation

HRID 1031915 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].[I:15]Cl>C(O)(=O)C>[I: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 24640Iodine chlorideHCID 27861435,6-Dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1,2-dione

Product 1

HCID 14988432HCID 14988432, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1,2dione (5 g) and iodine monochloride (5 g) in acetic acid (30 ml) was refluxed for 5 hours. After cooling, the mixture was poured into ice water and extracted with chloroform. The extract was washed with water, saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution successively and then dried over anhydrous sodium sulfate. Evaporation of chloroform afforded the title compound. The compound was recrystallized from ethanol to give 6.2 g (73.8%) as dark red needles.

Workup

  1. temperaturewas refluxed for 5 hours
  2. temperatureAfter cooling
  3. extractionextracted with chloroform
  4. washThe extract was washed with water, saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution successively
  5. dry with materialdried over anhydrous sodium sulfate
  6. customEvaporation of chloroform

Sources & evidence

ORD record
ord-ed58998be48e4b138aa61850249aadbc
Source dataset
uspto-grants-1990_09
Patent number
US04956372

Reaction notes

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