Water → HCID 23153898, compound

HRID 1175800Notes

Reaction equation

HRID 1175800 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:9]2[CH:13]=[C:12]([CH:14]=[O:15])[C:11]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[N+:22]([O-:24])=[O:23])=[N:10]2)[CH:6]=[CH:7][CH:8]=1.O.[Mn]([O-])(=O)(=O)=[O:27].[K+]>N1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:9]2[CH:13]=[C:12]([C:14]([OH:27])=[O:15])[C:11]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[N+:22]([O-:24])=[O:23])=[N:10]2)[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 962WaterHCID 516875Potassium PermanganateHCID 23153988HCID 23153988, compound

Product 1

HCID 23153898HCID 23153898, compoundYield 64.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a mixture of 1-(3-methoxyphenyl)-3-(2-nitrophenyl)-1H-pyrazole-4-carbaldehyde (1.00 g), water (2 ml) and pyridine (2 ml) was added portionwise potassium permanganate (538 mg). After stirring for 1 hour, the precipitated manganese oxide was filtered off through Celite, the Celite layer was washed with 1N aqueous sodium hydroxide solution. The filtrate and washings were combined, washed with ethyl acetate. The aqueous layer was acidified with 6N hydrochloric acid, extracted with ethyl acetate. The extract was washed with water and brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, the residue was solidified by adding hexane. The solid was collected by filtration and washed with hexane to obtain the target compound (676 mg).

Workup

  1. filtrationthe precipitated manganese oxide was filtered off through Celite
  2. washthe Celite layer was washed with 1N aqueous sodium hydroxide solution
  3. washwashed with ethyl acetate
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with water and brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationThe solvent was distilled off under reduced pressure
  8. additionby adding hexane
  9. filtrationThe solid was collected by filtration
  10. washwashed with hexane

Sources & evidence

ORD record
ord-89debf27d5854ead8c09d512830d3d2a
Source dataset
uspto-grants-2010_11
Patent number
US07842701B2

Reaction notes

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