3-(3-chloro-4-nitro-1H-pyrazol-1-yl)pyridine → 3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-amine

HRID 1773182Notes

Reaction equation

[Cl:1][C:2]1[C:6]([N+:7]([O-])=O)=[CH:5][N:4]([C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)[N:3]=1>[Pd].CO>[Cl:1][C:2]1[C:6]([NH2:7])=[CH:5][N:4]([C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)[N:3]=1

Participants

Conditions

Temperature: 20 °C

Procedure

A suspension of 3-(3-chloro-4-nitro-1H-pyrazol-1-yl)pyridine (1.00 g, 4.45 mmol) and palladium on carbon (10 wt %, 0.05 g, 0.467 mmol) in methanol (20 mL) was purged with nitrogen (N2) three times, followed by hydrogen three times. The reaction was stirred at 20° C. under 40 psi of hydrogen for 4 hours. After which time the reaction was purged with nitrogen three times and analyzed by thin layer chromatography [Eluent: 10% methanol/dichloromethane], which indicated that the reaction was complete. The reaction mixture was filtered through a Celite® pad and the pad was rinsed with methanol (2×10 mL). The filtrates were concentrated to dryness to afford a slightly pink solid (0.82 g, 95%). The spectral characterization was in agreement with the product prepared previously.

Workup

customwas purged with nitrogen (N2) three times
customAfter which time the reaction was purged with nitrogen three times
filtrationThe reaction mixture was filtered through a Celite® pad
washthe pad was rinsed with methanol (2×10 mL)
concentrationThe filtrates were concentrated to dryness

Sources & evidence

ORD record: ord-1ea07cb4397c41b5b0ed0e7c98657ef7
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09255083B2

Reaction notes

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