Ethylene Glycol → 5-(4-Nitrophenylsulfonyl)isoquinoline

HRID 619716Notes

Reaction equation

HRID 619716 reaction equation
[CH:1]1[C:10]2[CH:9]=[CH:8][CH:7]=[C:6]([S:11]([O-:13])=[O:12])[C:5]=2[CH:4]=[CH:3][N:2]=1.[Na+].F[C:16]1[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=1.C(O)CO>O>[N+:22]([C:19]1[CH:20]=[CH:21][C:16]([S:11]([C:6]2[CH:7]=[CH:8][CH:9]=[C:10]3[C:5]=2[CH:4]=[CH:3][N:2]=[CH:1]3)(=[O:13])=[O:12])=[CH:17][CH:18]=1)([O-:24])=[O:23]

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 9590p-FluoronitrobenzeneHCID 23707901HCID 23707901, compound

Product 1

HCID 154356855-(4-Nitrophenylsulfonyl)isoquinolineYield 20.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of sodium 5-isoquinolinesulfinate 100 mg (0.5 mmol), 4-fluoronitrobenzene 70 mg (0.5 mmol), ethylene glycol 0.1 ml and ethyleneglycoldiethylether 0.1 ml was heated and refluxed for 3.5 hours. Water was added to the reaction mixture, and the solution was extracted with ethyl acetate, the organic layer washed with a saturated sodium chloride, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was recrystallized from methanol to give 5-(4-nitrophenylsulfonyl)isoquinoline 30 mg (20.3%).

Workup

  1. temperaturewas heated
  2. temperaturerefluxed for 3.5 hours
  3. extractionthe solution was extracted with ethyl acetate
  4. washthe organic layer washed with a saturated sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was recrystallized from methanol

Sources & evidence

ORD record
ord-ad8652bc6bb849cb9ac2e259b15456fd
Source dataset
uspto-grants-1999_09
Patent number
US05959107

Reaction notes

Loading…