Ammonium Hydroxide → (1-Cyanocyclohexyl)acetic acid

HRID 1862579Notes

Reaction equation

HRID 1862579 reaction equation
[C:1]([C:3]1([CH2:9][C:10]([OH:12])=[O:11])[CH:8]=[CH:7][CH2:6][CH:5]=[CH:4]1)#[N:2].[NH4+].[OH-]>[Pd].CO>[C:1]([C:3]1([CH2:9][C:10]([OH:12])=[O:11])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1)#[N:2]

Participants

5

Reactant 2

HCID 14923Ammonium HydroxideHCID 18620044HCID 18620044, compound

Product 1

HCID 11073797(1-Cyanocyclohexyl)acetic acidYield 94%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Added 5% Pd/C catalyst (0.65 g, 0.31 mmol) to a solution of (1-cyanocyclohexa-2,5-dienyl)acetic acid (0.50 g, 3.1 mmol) and 28% NH4OH (42.5 μL, 38.3 μg, 0.31 mmol) in MeOH (15 mL). After shaking the reaction mixture under 50 psi H2 at room temperature for 1 hour, the pressure was slowly released. The reaction was filtered and concentrated under reduced pressure to afford 0.48 g (94%) of crude product.

Workup

  1. filtrationThe reaction was filtered
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-94df883e81504c9c9a4eac965709f451
Source dataset
uspto-grants-2003_03
Patent number
US06538148B2

Reaction notes

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