Hydrazine hydrate (1:1) → HCID 2805464, compound

HRID 1296939Notes

Reaction equation

HRID 1296939 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10](=O)[CH3:11])=[CH:5][CH:4]=1.COC(OC)[N:16]([CH3:18])C.O.[NH2:22]N>C(O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:18]=[N:16][NH:22][C:10]=2[CH3:11])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 312311-(p-Methoxyphenyl)-2-propanoneHCID 78373Dimethylformamide dimethyl acetal

Product 1

HCID 2805464HCID 2805464, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To p-Methoxy phenylacetone (1 eq) was added dimethylformamide dimethylacetal (1.5 eq) and the mixture was stirred at reflux overnight. The reaction was cooled to room temperature and diluted with ethanol. Hydrazine hydrate was added (3 eq) and all was heated to 85° C. over night. Once cooled the reaction mixture was concentrated in vacuo and partitioned between EtOAc and water. The organic phase was dried over MgSO4, filtered and concentrated in vacuo to give 4-(4-methoxy-phenyl)-5-methyl-1H-pyrazole as a white solid.

Workup

  1. temperatureat reflux overnight
  2. temperatureall was heated to 85° C. over night
  3. temperatureOnce cooled the reaction mixture
  4. concentrationwas concentrated in vacuo
  5. custompartitioned between EtOAc and water
  6. dry with materialThe organic phase was dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-61b2dc79a99e4261a5c79ae3020ec216
Source dataset
uspto-grants-2007_07
Patent number
US07247734B2

Reaction notes

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