Hydrazine → HCID 47002771, compound

HRID 600994Notes

Reaction equation

HRID 600994 reaction equation
[N+:1]([C:4]1[CH:8]=[CH:7][N:6]([CH2:9][C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)[N:5]=1)([O-])=O.NN>CO.C(OCC)(=O)C.[Ni].O>[N:12]1[CH:13]=[CH:14][CH:15]=[C:10]([CH2:9][N:6]2[CH:7]=[CH:8][C:4]([NH2:1])=[N:5]2)[CH:11]=1

Participants

7

Reactant 2

HCID 9321HydrazineHCID 67482386HCID 67482386, compound

Product 1

HCID 47002771HCID 47002771, compoundYield 75.1%

Reagents, catalysts & solvents 4

HCID 935NickelCatalystHCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-(3-Nitro-pyrazol-1-ylmethyl)-pyridine (113 mg, 0.55 mmol) was dissolved in a mixture of methanol and ethyl acetate (1 mL each). Hydrazine (156 μL, 4.97 mmol) was added followed by a slurry of Raney nickel in water (1.5 mL) causing vigorous gas evolution. After stirring 1 h, the reaction mixture was filtered and evaporated in vacuo. The residue was purified by flash column chromatography (Merck silica gel 60, 40-63 μm; 3% methanol/chloroform) to afford 1-pyridin-3-ylmethyl-1H-pyrazol-3-ylamine (72 mg, 75%) as a white solid: LC-MS (ESI) m/e calcd for C9H10N4 [M+] 174.09, found 175 [M+H+].

Workup

  1. filtrationthe reaction mixture was filtered
  2. customevaporated in vacuo
  3. customThe residue was purified by flash column chromatography (Merck silica gel 60, 40-63 μm; 3% methanol/chloroform)

Sources & evidence

ORD record
ord-0b9ebe9715034e6cb0229e5574ab58da
Source dataset
uspto-grants-2011_03
Patent number
US07902248B2

Reaction notes

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