Phenylhydrazine → HCID 23299993, compound

HRID 1253482Notes

Reaction equation

[CH:1]1([C:4](=O)/[CH:5]=[CH:6]/N(C)C)[CH2:3][CH2:2]1.[C:11]1([NH:17][NH2:18])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C(O)C>[CH:1]1([C:4]2[CH:5]=[CH:6][N:17]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[N:18]=2)[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 150 °C

Procedure

(2E)-1-cyclopropyl-3-(dimethylamino)prop-2-en-1-one (327 mg, 2.35 mmol) and phenylhydrazine (0.35 ml, 3.5 mmol) were added to ethanol (5 ml). The reaction mixture was heated to 150° C. in the Biotage Initiator Series microwave reactor. 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 3-cyclopropyl-1-phenyl-1H-pyrazole (faster eluting isomer) and 5-cyclopropyl-1-phenyl-1H-pyrazole (slower eluting isomer).

Workup

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

Sources & evidence

ORD record: ord-6e96274bf67e4624a7a77ef59d2d4bcc
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08455477B2

Reaction notes

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