Sodium Hydroxide → HCID 15435688, compound

HRID 619720Notes

Reaction equation

HRID 619720 reaction equation
[CH:1]1[C:10]2[C:5](=[C:6]([S:11][C:12]3[CH:13]=[CH:14][C:15]([N+:19]([O-:21])=[O:20])=[C:16]([CH:18]=3)[NH2:17])[CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1.[Mn]([O-])(=O)(=O)=[O:23].[K+].[OH-:28].[Na+]>S(=O)(=O)(O)O.C(O)(=O)C>[CH:1]1[C:10]2[C:5](=[C:6]([S:11]([C:12]3[CH:13]=[CH:14][C:15]([N+:19]([O-:21])=[O:20])=[C:16]([CH:18]=3)[NH2:17])(=[O:23])=[O:28])[CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 516875Potassium PermanganateHCID 21846955HCID 21846955, compound

Product 1

HCID 15435688HCID 15435688, compoundYield 17.9%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 1118Sulfuric AcidSolvent

Conditions

Temperature
0 °C

Procedure

5-(5-Isoquinolylsulfanyl)-2-nitroaniline 300 mg (1.0 mmol) was dissolved in a mixture solution of 5% sulfuric acid 2 ml and acetic acid 6 ml, potassium permanganate 200 mg (1.3 mmol) was added in an ice bath, and the mixture was stirred for 3 hours at 0° C. After stirring at room temperature for 3 hours, the mixture was neutralized with 2N sodium hydroxide and extracted with ethyl acetate (70 ml×3). The organic layer was dried over potassium carbonate, and concentrated under reduced pressure. The resulting residue was recrystalized from methanol-water to give 5-(5-isoquinolylsulfonyl)-2-nitroaniline 59 mg (17.9%).

Workup

  1. additionwas added in an ice bath
  2. stirringAfter stirring at room temperature for 3 hours
  3. extractionextracted with ethyl acetate (70 ml×3)
  4. dry with materialThe organic layer was dried over potassium carbonate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was recrystalized from methanol-water

Sources & evidence

ORD record
ord-1cf9f2972d4e4c5392730a9e4c4a8656
Source dataset
uspto-grants-1999_09
Patent number
US05959107

Reaction notes

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