p-Toluenesulfonic acid → HCID 86749528, compound

HRID 259781Notes

Reaction equation

HRID 259781 reaction equation
[C:1]([CH2:3][C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][CH:13]=1)[C:7]([O:9][CH3:10])=[O:8])#[N:2].[C:14]1([CH3:24])[CH:19]=[CH:18][C:17]([S:20]([OH:23])(=[O:22])=[O:21])=[CH:16][CH:15]=1>CO.[Pd]>[NH2:2][CH2:1][CH2:3][C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][CH:13]=1)[C:7]([O:9][CH3:10])=[O:8].[CH3:24][C:14]1[CH:19]=[CH:18][C:17]([S:20]([OH:23])(=[O:22])=[O:21])=[CH:16][CH:15]=1

Participants

5

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 10821136Methyl 3-(cyanomethyl)benzoate

Product 1

HCID 86749528HCID 86749528, compoundYield 112.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Nitrile 91a (4.8 g, 27 mmol) was hydrogenated on a Parr shaker at 40 psi H2 in the presence of 10% Pd/C (0.48 g) and p-toluenesulfonic acid (5.2 g, 27 mmol) in methanol (100 mL). The solution was filtered through a Celite pad to remove the catalyst, then solvent was removed in vacuo to give an orange solid (10.7 g). HR-MS: Calc'd. 180.1025. Found 180.1025.

Workup

  1. filtrationThe solution was filtered through a Celite pad
  2. customto remove the catalyst
  3. customsolvent was removed in vacuo

Sources & evidence

ORD record
ord-9000fc0e872f4edb86879bd0657b2bf8
Source dataset
uspto-grants-1996_06
Patent number
US05523302

Reaction notes

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