Benzoylacetonitrile → 1-(2-methylphenyl)-3-phenyl-1H-pyrazol-5-amine

HRID 63247

Reaction equation

[C:1]([CH2:9][C:10]#[N:11])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[C:13]1([CH3:21])[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[NH:19][NH2:20]>CO>[C:2]1([C:1]2[CH:9]=[C:10]([NH2:11])[N:19]([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[CH3:21])[N:20]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 120 °C

Procedure

Benzoylacetonitrile (500 mg, 3.44 mmol) and o-tolylhydrazine hydrochloride (574 mg, 3.61 mmol) were placed in a microwave vial and dissolved in methanol (1.7 mL). The reaction vessel was sealed, placed in a microwave oven and heated at 120° C. for 1 hour. After this period, the reaction mixture was concentrated onto silica gel and purified by flash chromatography (0-50% ethyl acetate/hexanes gradient) to afford the desired intermediate, 5-phenyl-2-o-tolyl-2H-pyrazol-3-ylamine (392 mg). LC/MS: Calc. C16H15N3 249.13 amu; Obs. [M+H]+=250.2 amu.

Workup

customThe reaction vessel was sealed
customplaced in a microwave oven
waitAfter this period
concentrationthe reaction mixture was concentrated onto silica gel
custompurified by flash chromatography (0-50% ethyl acetate/hexanes gradient)

Sources & evidence

ORD record: ord-463d2c9fe0064459b0b0a809e8778bb7
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09447058B2

Linked notes

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