Ammonia → HCID 58495614, compound

HRID 1190959Notes

Reaction equation

HRID 1190959 reaction equation
[CH3:1][C:2]([CH3:15])([CH3:14])[CH2:3][S:4][CH2:5][C:6]1[N:11]=[CH:10][C:9]([C:12]#[N:13])=[CH:8][CH:7]=1.N>[Ni].C(O)C>[NH2:13][CH2:12][C:9]1[CH:10]=[N:11][C:6]([CH2:5][S:4][CH2:3][C:2]([CH3:15])([CH3:14])[CH3:1])=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 58495693HCID 58495693, compound

Product 1

HCID 58495614HCID 58495614, compoundYield 105.1%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent2×

Procedure

To a slurry of Raney Nickel (0.5 g, 50% in water) in ethanol (100 mL) add a solution of 6-[(2,2-dimethylpropyl)thiomethyl]-pyridine-3-carbonitrile (1 g) in ethanol (10 mL) followed by aqueous ammonia (0.88 M, 5 mL) and hydrogenate the mixture in a Parr shaker at 60 psi for 3 h. Filter the mixture through Celite® washing the filter cake with ethanol (50 mL). Remove the solvent in vacuo to obtain the title compound as a colourless oil (1.07 g, 100%).

Workup

  1. customfor 3 h
  2. filtrationFilter the mixture through Celite®
  3. washwashing the filter cake with ethanol (50 mL)
  4. customRemove the solvent in vacuo

Sources & evidence

ORD record
ord-817a5218771543cdb3e6895550b8d785
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

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