Water → 5-(4-Nitrophenylsulfonyl)isoquinoline

HRID 619714Notes

Reaction equation

HRID 619714 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10][C:11]2[CH:20]=[CH:19][CH:18]=[C:17]3[C:12]=2[CH:13]=[CH:14][N:15]=[CH:16]3)=[CH:6][CH:5]=1)([O-:3])=[O:2].OOS([O-])=O.[K+].[OH-:27].[Na+].[OH2:29]>S(=O)(=O)(O)O>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([S:10]([C:11]2[CH:20]=[CH:19][CH:18]=[C:17]3[C:12]=2[CH:13]=[CH:14][N:15]=[CH:16]3)(=[O:29])=[O:27])=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 154356845-(4-Nitrophenylsulfanyl)isoquinolineHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 154356855-(4-Nitrophenylsulfonyl)isoquinolineYield 88.8%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

5-(4-Nitrophenylsulfanyl)isoquinoline 2.01 g (7.1 mmol) was dissolved in concentrated sulfuric acid 20 ml, OXONE (trademark) 10.80 g (17.6 mmol) was added in portions, and the mixture was stirred at room temperature for 1 hour. After water was added to the reaction mixture, the solution was neutralized with a solution of 4 N sodium hydroxide in water and extracted with ethyl acetate. The organic layer was washed with a saturated sodium chloride, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was recrystallized from ethyl acetate-hexane to give 5-(4-nitrophenylsulfonyl)isoquinoline 1.99 g (88.8%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with a saturated sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-735ebaf1e2ee4dab82229e1f73463e9b
Source dataset
uspto-grants-1999_09
Patent number
US05959107

Reaction notes

Loading…