Phenylhydrazine → HCID 67207603, compound

HRID 1253477Notes

Reaction equation

HRID 1253477 reaction equation
C[N:2](/[CH:4]=[C:5](/[C:10](=O)[CH2:11][CH3:12])\[C:6]([O:8][CH3:9])=[O:7])C.[C:14]1([NH:20]N)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(O)C>[CH2:11]([C:10]1[N:20]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:2]=[CH:4][C:5]=1[C:6]([O:8][CH3:9])=[O:7])[CH3:12]

Participants

4

Reactant 2

HCID 7516PhenylhydrazineHCID 21807119HCID 21807119, compound

Product 1

HCID 67207603HCID 67207603, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
150 °C

Procedure

Methyl (2Z)-2-[(dimethylamino)methylene]-3-oxopentanoate (383 mg, 2.07 mmol) and phenylhydrazine (0.308 ml, 3.10 mmol) were added to ethanol (4 ml). The reaction mixture was heated to 150° C. in the Biotage Initiator Series microwave. After 30 minutes, the reaction mixture was cooled and concentrated. The residue was purified by column chromatography on silica gel (ethyl acetate/hexanes gradient) to afford methyl 5-ethyl-1-phenyl-1H-pyrazole-4-carboxylate.

Workup

  1. temperaturethe reaction mixture was cooled
  2. concentrationconcentrated
  3. customThe residue was purified by column chromatography on silica gel (ethyl acetate/hexanes gradient)

Sources & evidence

ORD record
ord-50f482caa8b44c6dab9701429a073d0c
Source dataset
uspto-grants-2013_06
Patent number
US08455477B2

Reaction notes

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