Potassium Permanganate → methyl 3-chloro-1-(pyridin-3-yl)-1H-pyrazole-5-carboxylate
Reaction equation
[Cl:1][C:2]1[CH2:6][CH:5]([C:7]([O:9][CH3:10])=[O:8])[N:4]([C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)[N:3]=1.[Mn]([O-])(=O)(=O)=O.[K+]>CC(C)=O>[Cl:1][C:2]1[CH:6]=[C:5]([C:7]([O:9][CH3:10])=[O:8])[N:4]([C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)[N:3]=1Participants
Procedure
Methyl 3-chloro-1-(pyridine-3-yl)-4,5-dihydro-1H-pyrazole-5-carboxylate (0.500 g, 2.09 mmol) was stirred in acetone (10 mL). potassium permanganate (0.330 g, 2.09 mmol) was added in one portion and the reaction was stirred at room temperature overnight, at which point thin layer chromatography analysis (70% ethyl acetate/hexanes) indicated that the reaction was <50% complete. Additional potassium permanganate (520 mg, 3.29 mmol) was added and the reaction was stirred for an additional 4 hours. The mixture was filtered and concentrated and the residue was partitioned between ethyl acetate and water. The organic portion was dried over sodium sulfate, filtered, and concentrated. The residue was purified flash column chromatography using 80-100% ethyl acetate/hexanes as eluent to provide the desired product as a white solid (180 mg 36%).
Workup
- filtrationThe mixture was filtered
- concentrationconcentrated
- customthe residue was partitioned between ethyl acetate and water
- dry with materialThe organic portion was dried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated
- customThe residue was purified flash column chromatography
Sources & evidence
- ORD record
- ord-f2ddeeadbdf249a88029cf7238abdcc5
- Source dataset
- uspto-grants-2016_02
- Patent number
- US09255083B2
Reaction notes
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