Sodium Hydroxide → HCID 21846995, compound

HRID 619717Notes

Reaction equation

HRID 619717 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([C:13]2[CH:22]=[CH:21][CH:20]=[C:19]3[C:14]=2[CH:15]=[CH:16][N:17]=[CH:18]3)(=[O:12])=[O:11])=[CH:6][CH:5]=1)([O-])=O.[OH-].[Na+]>Cl.O>[CH:18]1[C:19]2[C:14](=[C:13]([S:10]([C:7]3[CH:8]=[CH:9][C:4]([NH2:1])=[CH:5][CH:6]=3)(=[O:12])=[O:11])[CH:22]=[CH:21][CH:20]=2)[CH:15]=[CH:16][N:17]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 154356855-(4-Nitrophenylsulfonyl)isoquinoline

Product 1

HCID 21846995HCID 21846995, compoundYield 76.5%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

5-(4-Nitrophenylsulfonyl)isoquinoline 160 mg (0.6 mmol) was dissolved in concentrated hydrochloric acid 170 ml, stannous chloride dihydrate 650 mg (2.9 mmol) was added, and the mixture was stirred overnight at room temperature. 4 N sodium hydroxide in water was added to the reaction solution, and the resulting alkaline solution was extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was recrystallized from methanol to give 4-(5-isoquinolylsulfonyl)aniline 110 mg (76.5%).

Workup

  1. extractionthe resulting alkaline solution was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was recrystallized from methanol

Sources & evidence

ORD record
ord-5925996de9cc46f8bfd78c01cde72ea5
Source dataset
uspto-grants-1999_09
Patent number
US05959107

Reaction notes

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