Acetone → 1-(3,5-dichloropyridin-2-yl)-3-(trifluoromethyl)-1H-pyrazole-5-carboxylic acid

HRID 453072Notes

Reaction equation

[Cl:1][C:2]1[C:3]([N:9]2[C:13]([C:14]3[O:15]C=CC=3)=[CH:12][C:11]([C:19]([F:22])([F:21])[F:20])=[N:10]2)=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1.CC(C)=[O:25].[Mn]([O-])(=O)(=O)=O.[K+]>O>[Cl:1][C:2]1[C:3]([N:9]2[C:13]([C:14]([OH:15])=[O:25])=[CH:12][C:11]([C:19]([F:22])([F:21])[F:20])=[N:10]2)=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

Conditions

Temperature: 65 °C

Procedure

To a 100 mL flask, 3,5-dichloro-2-(5-(furan-2-yl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)pyridine (1.47 g, 4.22 mmol), acetone (10 mL) and a solution (10 mL) of potassium permanganate (3.33 g, 21.1 mmol) in water were added. The reaction mixture was heated to 65° C. for 4 hours and cooled to room temperature, then isolated via filtration, a cake is obtained. The cake was washed with hot solution of potassium hydroxide. To the filtrate was added ethyl acetate (80 mL), water (100 mL) and partitioned. The aqueous layer was acidified with concentrated hydrochloric acid to pH of 2-3, and extracted with ethyl acetate (200 mL). The organic extracts were washed with saturated brine (100 mL), dried over anhydrous magnesium sulfate and concentrated by rotary evaporator to give the product (0.80 g) as yellow oil in 58% yield.

Workup

temperaturecooled to room temperature
customisolated via filtration
customa cake is obtained
washThe cake was washed with hot solution of potassium hydroxide
additionTo the filtrate was added ethyl acetate (80 mL), water (100 mL)
custompartitioned
extractionextracted with ethyl acetate (200 mL)
washThe organic extracts were washed with saturated brine (100 mL)
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated by rotary evaporator

Sources & evidence

ORD record: ord-ddffe143a71d4d4baf9c57831b8ec904
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08492409B2

Reaction notes

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