HCID 22014398, compound → HCID 22014388, compound

HRID 1532766Notes

Reaction equation

HRID 1532766 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[N:9])=[C:4]([CH2:10][CH:11]=[CH2:12])[C:3]=1[OH:13].[H][H]>[Pd].C(OCC)(=O)C>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[N:9])=[C:4]([CH2:10][CH2:11][CH3:12])[C:3]=1[OH:13]

Participants

5

Reactant 2

HCID 22014398HCID 22014398, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22014388HCID 22014388, compoundYield 283.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-amino-5-cyano-6-prop-1-ene-3-yl-phenol (0.5 g, 2.4 mmol) and 10% palladium on carbon (0.05 g) in ethyl acetate (50 mL) was stirred at rt under 1 atm of hydrogen for 2 hours. The mixture was filtered through Celite to remove the palladium and the filtrate was concentrated under reduced pressure to afford the title compound as a pinkish-white solid (1.2 g, 78%). MS(ES+) m/e 177 [M+H]+; MS(ES−) m/e 175[M−H]−.

Workup

  1. filtrationThe mixture was filtered through Celite
  2. customto remove the palladium
  3. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-3392180e29b04fefb367f6b448a2ac14
Source dataset
uspto-grants-2001_03
Patent number
US06204294B1

Reaction notes

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