1,3-Dimethyl-1H-pyrazole-5-carbonitrile → (1,3-Dimethyl-1H-pyrazol-5-yl)methanamine

HRID 1827504Notes

Reaction equation

HRID 1827504 reaction equation
[CH3:1][N:2]1[C:6]([C:7]#[N:8])=[CH:5][C:4]([CH3:9])=[N:3]1>[Pd].C(O)C>[CH3:1][N:2]1[C:6]([CH2:7][NH2:8])=[CH:5][C:4]([CH3:9])=[N:3]1

Participants

4

Reactant 1

HCID 27362971,3-Dimethyl-1H-pyrazole-5-carbonitrile

Product 1

HCID 1257670(1,3-Dimethyl-1H-pyrazol-5-yl)methanamineYield 90%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A suspension of 2,5-Dimethyl-2H-pyrazole-3-carbonitrile (654 mg, 5.4 mmol) and 10% palladium on carbon (200 mg) in ethanol (15 mL) was shaken in a Parr hydrogenation apparatus under 45 psi H2 for 17 hr. The mixture was filtered through celite and the filtrate was concentrated under reduced pressure to give 608 mg of an oil which was used without any further purification. 1H NMR (CDCl3) δ 5.91 (1H, s), 3.81, 3.73 (2H,2s), 3.75 (3H, s), 2.21 (3H, s).

Workup

  1. filtrationThe mixture was filtered through celite
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-5774c3dfd7d147e1ba0495209d37260a
Source dataset
uspto-grants-2006_05
Patent number
US07053107B2

Reaction notes

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