Acetic Acid → 5-[4-(Pyrrole-1-yl)phenylsulfonyl]isoquinoline

HRID 619719Notes

Reaction equation

HRID 619719 reaction equation
[CH:1]1[C:10]2[C:5](=[C:6]([S:11]([C:14]3[CH:20]=[CH:19][C:17]([NH2:18])=[CH:16][CH:15]=3)(=[O:13])=[O:12])[CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1.CO[CH:23]1[CH2:27][CH2:26][CH:25](OC)O1.C(O)(=O)C>O>[N:18]1([C:17]2[CH:19]=[CH:20][C:14]([S:11]([C:6]3[CH:7]=[CH:8][CH:9]=[C:10]4[C:5]=3[CH:4]=[CH:3][N:2]=[CH:1]4)(=[O:13])=[O:12])=[CH:15][CH:16]=2)[CH:23]=[CH:27][CH:26]=[CH:25]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 790982,5-DimethoxytetrahydrofuranHCID 21846995HCID 21846995, compound

Product 1

HCID 154356875-[4-(Pyrrole-1-yl)phenylsulfonyl]isoquinolineYield 83%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture solution of 4-(5-isoquinolylsulfonyl)aniline 300 mg (1.1 mmol), 2,5-dimethoxytetrahydrofuran 160 mg (1.2 mmol) and acetic acid 2 ml was heated and refluxed for 1 hour. Water was added to the reaction solution, and the solution was extracted with ethyl acetate. The organic layer was washed with saturated sodium hydrogencarbonate and saturated sodium chloride, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was recrystalized from ethyl acetate-hexane to give 5-[4-(pyrrole-1-yl)phenylsulfonyl]isoquinoline 280 mg (83.0%).

Workup

  1. temperaturerefluxed for 1 hour
  2. extractionthe solution was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated sodium hydrogencarbonate and saturated sodium chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was recrystalized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-fe7d96626de2409792c31fcfa65077d4
Source dataset
uspto-grants-1999_09
Patent number
US05959107

Reaction notes

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