Potassium Permanganate → HCID 25059379, compound

HRID 2089121Notes

Reaction equation

HRID 2089121 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-a108e860534e4a9e89c4909ffcbb3a0c
Source dataset
uspto-grants-2013_05
Patent number
US08436022B2

Reaction notes

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