HCID 21446165, compound → HCID 21446148, compound

HRID 597735Notes

Reaction equation

HRID 597735 reaction equation
[C:1]([C:3]1([CH2:11][CH2:12][C:13]#[N:14])[CH2:8][CH:7]2[CH2:9][CH2:10][CH:4]1[CH:5]=[CH:6]2)#[N:2]>CO.[Pd]>[C:1]([C:3]1([CH2:11][CH2:12][C:13]#[N:14])[CH2:8][CH:7]2[CH2:9][CH2:10][CH:4]1[CH2:5][CH2:6]2)#[N:2]

Participants

4

Reactant 1

HCID 21446165HCID 21446165, compound

Product 1

HCID 21446148HCID 21446148, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

An amount of 128.7 g (0.69 mole) of 2-cyano-bicyclo[2.2.2]oct-5-ene-2-propionitrile is dissolved in 1.3 liters of the purest methanol; an addition is then made of 3 g of palladium charcoal (5% Pd) and hydrogenation performed at 15°-25° under normal pressure to effect a hydrogen absorption of 90% of theory. After removal by filtration of the catalyst, the solvent is evaporated off and the residue fractionated to obtain 2-cyano-bicyclo[2.2.2]octane-2-propionitrile, B.P. 114°-116°/0.01 Torr.

Workup

  1. additionan addition
  2. customperformed at 15°-25° under normal pressure
  3. customa hydrogen absorption of 90% of theory
  4. customAfter removal
  5. filtrationby filtration of the catalyst
  6. customthe solvent is evaporated off

Sources & evidence

ORD record
ord-9fae928e5a604a10950676288a1eda57
Source dataset
uspto-grants-1977_03
Patent number
US04015007

Reaction notes

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