HCID 54438508, compound → HCID 53886899, compound

HRID 845693Notes

Reaction equation

HRID 845693 reaction equation
[C:1]([N:3]([CH2:23][CH2:24][CH2:25][CH3:26])[C:4](=[O:22])[CH:5]([O:7][C:8]1[CH:13]=[CH:12][C:11]([O:14]CC2C=CC=CC=2)=[CH:10][CH:9]=1)[CH3:6])#[N:2].[H][H]>O1CCOCC1.[Pd]>[C:1]([N:3]([CH2:23][CH2:24][CH2:25][CH3:26])[C:4](=[O:22])[CH:5]([O:7][C:8]1[CH:9]=[CH:10][C:11]([OH:14])=[CH:12][CH:13]=1)[CH3:6])#[N:2]

Participants

5

Reactant 2

HCID 54438508HCID 54438508, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 53886899HCID 53886899, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

16.5 g (0.047 mole) of 2-(4-benzyloxyphenoxy)propionic acid N-cyano-N-butylamide, prepared according to Example (b), are hydrogenated with hydrogen in 170 ml of dioxan, in the presence of 1.7 g of 5% palladium on carbon catalyst. The catalyst is then removed by filtration and the filtrate is concentrated by evaporation. The residue is chromatographed through silica gel eluted with ethyl acetate/hexane (1:3), affording 7.5 g (61% of theory) of 2-(4-hydroxyphenoxy)propionic acid N-cyano-N-butylamide as a colourless oil. nD25 : 1.5132.

Workup

  1. customThe catalyst is then removed by filtration
  2. concentrationthe filtrate is concentrated by evaporation
  3. customThe residue is chromatographed through silica gel
  4. washeluted with ethyl acetate/hexane (1:3)

Sources & evidence

ORD record
ord-d82185622d4f43e6aab02fcce070a6c6
Source dataset
uspto-grants-1988_07
Patent number
US04759796

Reaction notes

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