N-Iodosuccinimide → HCID 23369570, compound

HRID 1900722Notes

Reaction equation

HRID 1900722 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH:10]1[O:23][C:13]2=[C:14]3[C:19](=[CH:20][CH:21]=[C:12]2[CH2:11]1)[NH:18][C:17](=[O:22])[CH:16]=[CH:15]3)=[O:7])([CH3:4])([CH3:3])[CH3:2].[I:24]N1C(=O)CCC1=O>C(Cl)(Cl)Cl.CO>[C:1]([O:5][C:6]([NH:8][CH2:9][CH:10]1[O:23][C:13]2=[C:14]3[C:19](=[C:20]([I:24])[CH:21]=[C:12]2[CH2:11]1)[NH:18][C:17](=[O:22])[CH:16]=[CH:15]3)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 120273N-Iodosuccinimide3×HCID 23369689HCID 23369689, compound

Product 1

HCID 23369570HCID 23369570, compoundYield 73.2%

Reagents, catalysts & solvents 1

HCID 21584188Chloroform methanolSolvent

Procedure

2-(t-Butoxycarbonyl)aminomethyl-2,3,6,7-tetrahydrofuro[2,3-f]quinoline-7-one (882 mg) and N-iodosuccinimide (756 mg) were dissolved in a solvent mixture (44 ml) of chloroform-methanol (5:1). After refluxing for 2.5 hours with heat, N-iodosuccinimide (756 mg) was added to the mixture, followed by further 2 hour refluxing with heat. Further, N-iodosuccinimide (400 mg) was added to the mixture, which was then refluxed for 1.5 hours with heat. After completion of the reaction, the solvent was distilled off, and the residue was purified by silica gel column chromatography (eluent=chloroform:methanol=200:1) to obtain 903 mg of 2-(t-butoxycarbonyl)aminomethyl-5-iodo -2,3,6,7-tetrahydrofuro[2,3-f]quinoline-7-one (73.2%). This compound was recrystallized from a solvent mixture of chloroform-n-hexane to obtain pale yellow powdery crystals (mp.: 173°-174° C.).

Workup

  1. temperatureAfter refluxing for 2.5 hours
  2. temperaturewith heat
  3. temperaturerefluxing
  4. temperaturewith heat
  5. temperaturewas then refluxed for 1.5 hours
  6. temperaturewith heat
  7. customAfter completion of the reaction
  8. distillationthe solvent was distilled off
  9. customthe residue was purified by silica gel column chromatography (eluent=chloroform:methanol=200:1)

Sources & evidence

ORD record
ord-ee9760d9ed994b9ea41970dac0a4b0bf
Source dataset
uspto-grants-1996_11
Patent number
US05576324

Reaction notes

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