Potassium Permanganate → CID 86697018

HRID 1775592Notes

Reaction equation

HRID 1775592 reaction equation
[Cl:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[N:6][N:5]=[C:4]2[N:14](C=C)[N:15]=[C:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:3]=12.[Mn]([O-])(=O)(=O)=O.[K+]>CC(C)=O>[Cl:1][C:2]1[C:7]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)=[N:6][N:5]=[C:4]2[NH:14][N:15]=[C:16]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:3]=12

Participants

4

Reactant 2

HCID 516875Potassium Permanganate2×HCID 665762544-chloro-3,5-diphenyl-1-vinyl-1H-pyrazolo[3,4-c]pyridazine

Product 1

HCID 86697018CID 86697018

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 4-chloro-3,5-diphenyl-1-vinyl-1H-pyrazolo[3,4-c]pyridazine (50 mg, 0.15 mmol) in acetone (5 mL) was added a 2% aqueous solution of potassium permanganate (71 mg, 0.45 mmol, 3.5 mL water) in one portion. The mixture was stirred at room temperature for 2 h, then another portion of potassium permanganate (12 mg, 0.075 mmol), was added and stirring continued for 15 min. The solids were filtered off and the filtrate was partitioned between water and CH2Cl2. The aqueous phase was re-extracted with CH2Cl2 and the combined organic layers were dried over MgSO4 and concentrated under reduced pressure. The crude 4-chloro-3,5-diphenyl-1H-pyrazolo[3,4-c]pyridazine (64 mg) was used directly in the following step.

Workup

  1. stirringstirring
  2. waitcontinued for 15 min
  3. filtrationThe solids were filtered off
  4. customthe filtrate was partitioned between water and CH2Cl2
  5. extractionThe aqueous phase was re-extracted with CH2Cl2
  6. dry with materialthe combined organic layers were dried over MgSO4
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a036ecef1fc14e74b8b99544fc5104e6
Source dataset
uspto-grants-2016_02
Patent number
US09260381B2

Reaction notes

Loading…