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

HRID 512713Notes

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-44f319e68c584118bdd8177d330b8372
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09102654B2

Reaction notes

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