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Water → 1-(2-Methoxyphenyl)-3,4,5-trimethyl-1H-pyrazole

HRID 337333
Notes
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Reaction equation

HRID 337333 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][NH2:11].[CH3:12][CH:13]([C:17](=O)[CH3:18])[C:14](=O)[CH3:15].O.C(=O)([O-])[O-].[Na+].[Na+]>C(O)C>[CH3:2][O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]1[C:17]([CH3:18])=[C:13]([CH3:12])[C:14]([CH3:15])=[N:11]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 699493-Methyl-2,4-pentanedioneHCID 28494452-Methoxyphenylhydrazine Hydrochloride

Product 1

HCID 552194401-(2-Methoxyphenyl)-3,4,5-trimethyl-1H-pyrazole

Reagents, catalysts & solvents 1

HCID 702Ethanol
Solvent

Procedure

200 mg of 2-methoxyphenyl hydrazine hydrochloride was dissolved in 4 ml of ethanol, and 134 μl of 3-methyl-2,4-pentanedione was added and heated at reflux for 3 hours. To the reaction mixture was added 50 ml of water, neutralized with a saturated aqueous solution of sodium carbonate, and extracted with 60 ml of ethyl acetate. After the organic layer was dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure to yield 209.8 mg of the title compound.

Workup

  1. temperatureheated
  2. temperatureat reflux for 3 hours
  3. extractionextracted with 60 ml of ethyl acetate
  4. dry with materialAfter the organic layer was dried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-6c70bd91c2274e9ba033fb8f22b7f8e0
Source dataset
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08889727B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes