2-Hydrazinopyridine → 1-(Pyridin-2-yl)-1H-pyrazol-3-amine

HRID 1504780Notes

Reaction equation

[NH:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1)[NH2:2].CO[CH:11]=[CH:12][C:13]#[N:14].[O-]CC.[Na+]>C(O)C>[N:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[N:1]1[CH:11]=[CH:12][C:13]([NH2:14])=[N:2]1

Participants

Conditions

Temperature: 80 °C

Procedure

2-Hydrazinylpyridine (100 mg, 0.92 mmol), 3-methoxyacrylonitrile (0.077 mL, 0.92 mmol) and sodium ethoxide (62 mg, 0.92 mmol) were dissolved in ethanol (4.5 mL) and stirred at 80° C. for 2 hours. The reaction mixture was cooled to room temperature, concentrated under reduced pressure, and purified by silica gel chromatography (ethyl acetate/hexanes, linear gradient) to afford 1-(pyridin-2-yl)-1H-pyrazol-3-amine. The purified material contained impurities and was used without further purification. MS ESI calc'd. for C8H9N4 [M+H]+ 161. found 161.

Workup

temperatureThe reaction mixture was cooled to room temperature
concentrationconcentrated under reduced pressure
custompurified by silica gel chromatography (ethyl acetate/hexanes, linear gradient)

Sources & evidence

ORD record: ord-1f2ebba0886b4a3abf08a66602c61bcf
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09216173B2

Reaction notes

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