Water → 5-(4-Nitrophenylsulfonyl)isoquinoline

HRID 619713Notes

Reaction equation

HRID 619713 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].[OH2:21].[OH-:22].[Na+]>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:22])=[O:21])=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 962Water2×HCID 14798Sodium HydroxideHCID 154356845-(4-Nitrophenylsulfanyl)isoquinoline

Product 1

HCID 154356855-(4-Nitrophenylsulfonyl)isoquinolineYield 63.6%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

5-(4-Nitrophenylsulfanyl)isoquinoline 100 mg (0.4 mmol) was dissolved in concentrated sulfuric acid 2.0 ml, Beckman's reagent 3.0 ml (a mixture of K2Cr2O7 1 g-H2SO4 1 ml-H2O 9 ml) was added dropwise, and the mixture was stirred at room temperature for 3 hours. After water was added to the reaction mixture, the solution was neutralized with 4 N sodium hydroxide, and precipitates were filtered, washed with water, and recrystallized from methanol to give 5-(4-nitrophenylsulfonyl)isoquinoline 70 mg (63.6%).

Workup

  1. additionwas added dropwise
  2. customprecipitates
  3. filtrationwere filtered
  4. washwashed with water
  5. customrecrystallized from methanol

Sources & evidence

ORD record
ord-7d275c82301a4f31900e46b27c616989
Source dataset
uspto-grants-1999_09
Patent number
US05959107

Reaction notes

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