Potassium Permanganate → HCID 25059379, compound

HRID 1430102Notes

Reaction equation

HRID 1430102 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:27][OH:28])[CH:5]=[N:6][C:7]=1[C:8]1[CH:13]=[CH:12][C:11]([C:14]2[NH:18][C:17]3[CH:19]=[C:20]([C:23]([F:26])([F:25])[F:24])[CH:21]=[CH:22][C:16]=3[N:15]=2)=[CH:10][CH:9]=1.[Mn]([O-])(=O)(=O)=[O:30].[K+]>N1C=CC=CC=1.O>[Cl:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][C:11]([C:14]3[NH:18][C:17]4[CH:19]=[C:20]([C:23]([F:25])([F:26])[F:24])[CH:21]=[CH:22][C:16]=4[N:15]=3)=[CH:10][CH:9]=2)=[N:6][CH:5]=[C:4]([CH:3]=1)[C:27]([OH:30])=[O:28]

Participants

5

Reactant 2

HCID 516875Potassium Permanganate2×HCID 25059128HCID 25059128, compound

Product 1

HCID 25059379HCID 25059379, compoundYield 77.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 1049PyridineSolvent

Procedure

0.40 g of {5-chloro-6-[4-(6-trifluoromethyl-1H-benzoimidazol-2-yl)-phenyl]-pyridin-3-yl}-methanol (28) (0.99 mmol) prepared in Example 16 was dissolved in 4 mL of pyridine and 2 mL of distilled water. 0.59 g of potassium permanganate (3.71 mmol) was added thereto, and reacted at 110° C. for 4 hours. Then, 0.59 g of potassium permanganate (3.71 mmol) and 2 mL of distilled water were added thereto, and reacted at 110° C. for 18 hours. The resultant was cooled to room temperature, and concentrated under reduced pressure. The aqueous layer was washed with ethyl acetate, pH 1 was adjusted with concentrated hydrochloric acid, and extracted with ethyl acetate several times. The organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The residue was separated by column chromatography (eluting solvent: chloroform/methanol=10/1) to obtain 0.32 g of 5-chloro-6-[4-(6-trifluoromethyl-1H-benzoimidazol-2-yl)-phenyl]-nicotinic acid (yield 77%).

Workup

  1. customreacted at 110° C. for 4 hours
  2. customreacted at 110° C. for 18 hours
  3. concentrationconcentrated under reduced pressure
  4. washThe aqueous layer was washed with ethyl acetate, pH 1
  5. extractionextracted with ethyl acetate several times
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was separated by column chromatography (eluting solvent: chloroform/methanol=10/1)

Sources & evidence

ORD record
ord-c91ba93fbcbd417480bb5ed8ec7fbd98
Source dataset
uspto-grants-2015_01
Patent number
US08940769B2

Reaction notes

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