Potassium Permanganate → HCID 67494358, compound

HRID 1256233Notes

Reaction equation

HRID 1256233 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[C:18]2[CH:17]=[C:16]([CH:19]=[O:20])[CH:15]=[CH:14][C:13]=2[C:12]2[N:21]([S:24]([N:27]([CH3:29])[CH3:28])(=[O:26])=[O:25])[N:22]=[CH:23][C:11]=2[N:10]=1.[Mn]([O-])(=O)(=O)=[O:31].[K+]>CC(C)=O.O>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[C:18]2[CH:17]=[C:16]([C:19]([OH:31])=[O:20])[CH:15]=[CH:14][C:13]=2[C:12]2[N:21]([S:24](=[O:25])(=[O:26])[N:27]([CH3:29])[CH3:28])[N:22]=[CH:23][C:11]=2[N:10]=1

Participants

5

Reactant 2

HCID 516875Potassium PermanganateHCID 86664931HCID 86664931, compound

Product 1

HCID 67494358HCID 67494358, compoundYield 99.7%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

A 250 ml round-bottomed flask is charged with 1.41 g of 5-(2,6-difluorophenyl)-7-formyl-N,N-dimethyl-1H-pyrazolo[4,3-c]isoquinoline-1-sulphonamide in 124 ml of acetone. 1.07 g of potassium permanganate in solution in 62 ml of water are added. After 1 h at RT, the acetone is evaporated and then the mixture is acidified to a pH of 1 by addition of 5N hydrochloric acid. The mixture is extracted with ethyl acetate and the organic phase is washed with saturated NaCl solution, dried over MgSO4, filtered and concentrated under RP to give 1.46 g of 5-(2,6-difluorophenyl)-1-(dimethylsulphamoyl)-1H-pyrazolo[4,3-c]isoquinoline-7-carboxylic acid (yellow solid). LC-MS-DAD-ELSD: 433 (+)=(M+H)(+).

Workup

  1. customthe acetone is evaporated
  2. additionthe mixture is acidified to a pH of 1 by addition of 5N hydrochloric acid
  3. extractionThe mixture is extracted with ethyl acetate
  4. washthe organic phase is washed with saturated NaCl solution
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under RP

Sources & evidence

ORD record
ord-58fa14cc463b4dcb811a4cc4e2cf252b
Source dataset
uspto-grants-2013_06
Patent number
US08461175B2

Reaction notes

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