Ammonia → HCID 58495659, compound

HRID 1190961Notes

Reaction equation

HRID 1190961 reaction equation
[CH3:1][C:2]1([CH3:17])[CH2:7][CH2:6][CH2:5][CH:4]([S:8][C:9]2[N:14]=[CH:13][C:12]([C:15]#[N:16])=[CH:11][CH:10]=2)[CH2:3]1.N>[Ni].C(O)C>[NH2:16][CH2:15][C:12]1[CH:13]=[N:14][C:9]([S:8][CH:4]2[CH2:5][CH2:6][CH2:7][C:2]([CH3:17])([CH3:1])[CH2:3]2)=[CH:10][CH:11]=1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 58495499HCID 58495499, compound

Product 1

HCID 58495659HCID 58495659, compoundYield 53.2%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent2×

Procedure

To a slurry of Raney Nickel (0.2 g, 50% in water) in ethanol (35 mL) add a solution of 6-[(3,3-dimethylcyclohexyl)thio]-pyridine-3-carbonitrile (0.37 g, 1.5 mmol) in ethanol (5 mL) followed by aqueous ammonia (0.88 M, 2 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. Remove the solvent in vacuo to obtain the title compound as an oil (0.2 g, 53%).

Workup

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

Sources & evidence

ORD record
ord-9b810b0ae730472abf3c0ede1c9975c5
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

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