3-[(3-Nitro-1H-pyrazol-1-yl)methyl]benzonitrile → 3-((3-Amino-1h-pyrazol-1-yl)methyl)benzonitrile

HRID 18958Notes

Reaction equation

HRID 18958 reaction equation
[N+:1]([C:4]1[CH:8]=[CH:7][N:6]([CH2:9][C:10]2[CH:11]=[C:12]([CH:15]=[CH:16][CH:17]=2)[C:13]#[N:14])[N:5]=1)([O-])=O>C(O)C.[Pd]>[NH2:1][C:4]1[CH:8]=[CH:7][N:6]([CH2:9][C:10]2[CH:11]=[C:12]([CH:15]=[CH:16][CH:17]=2)[C:13]#[N:14])[N:5]=1

Participants

4

Reactant 1

HCID 617213403-[(3-Nitro-1H-pyrazol-1-yl)methyl]benzonitrile

Product 1

HCID 607831823-((3-Amino-1h-pyrazol-1-yl)methyl)benzonitrileYield 64.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 3-(3-nitro-pyrazol-1-ylmethyl)-benzonitrile (507 mg, 2.22 mmol) in ethanol (25 mL) was hydrogenated in a Parr hydrogenator using 10% palladium on carbon (53 mg, 0.05 mmol) for 4 h at 50 psi at room temperature. The product was isolated, after filtration through a Celite plug, and purification by ISCO flash chromatography (Teledyne Isco RediSep Flash Column 4 g; 0% to 10% methanol/dichloromethane) to afford 3-(3-amino-pyrazol-1-ylmethyl)-benzonitrile, (283 mg, 64%) as light orange solid.

Workup

  1. customfor 4 h
  2. customat room temperature
  3. customThe product was isolated
  4. filtrationafter filtration
  5. customthrough a Celite plug, and purification by ISCO flash chromatography (Teledyne Isco RediSep Flash Column 4 g; 0% to 10% methanol/dichloromethane)

Sources & evidence

ORD record
ord-983251181e004aef93b38d02e17cf7f7
Source dataset
uspto-grants-2010_06
Patent number
US07741327B2

Reaction notes

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