Potassium Permanganate → HCID 67107203, compound

HRID 1623730Notes

Reaction equation

HRID 1623730 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][O:9][C:10]2[CH:24]=[CH:23][C:22]([CH:25]=[O:26])=[CH:21][C:11]=2[C:12]([NH:14][C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)=[O:13])=[CH:4][CH:3]=1.[Mn]([O-])(=O)(=O)=[O:28].[K+]>CC(C)=O.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][O:9][C:10]2[CH:24]=[CH:23][C:22]([C:25]([OH:28])=[O:26])=[CH:21][C:11]=2[C:12]([NH:14][C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)=[O:13])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 516875Potassium PermanganateHCID 86668208HCID 86668208, compound

Product 1

HCID 67107203HCID 67107203, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

To a solution of 2-{[(4-fluorophenyl)methyl]oxy}-5-formyl-N-3-pyridinylbenzamide (may be prepared as described in Example 82; 100 mg, 0.29 mmol) in acetone (10 ml) was added potassium permanganate (67.7 mg, 0.43 mmol) as a solution in 10 ml of water. The mixture was stirred at room temperature overnight. The mixture was quenched by adding 10 ml of 5% sodium sulfite solution. The solution was filtered through celite and mixed with 1 ml of acetic acid. The mixture was evaporated to a third volume, water (20 ml) was added and the mixture was filtered to yield the title compound as a white solid. This contains about 10% starting material and was used directly without further purification. 63 mg.

Workup

  1. customThe mixture was quenched
  2. additionby adding 10 ml of 5% sodium sulfite solution
  3. filtrationThe solution was filtered through celite
  4. additionmixed with 1 ml of acetic acid
  5. customThe mixture was evaporated to a third volume, water (20 ml)
  6. additionwas added
  7. filtrationthe mixture was filtered

Sources & evidence

ORD record
ord-df1b417ffca442e498ff96acbd0f2152
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

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