2-Furan-3-yl-5-hydroxy-benzonitrile → 3-Aminomethyl-4-furan-3-yl-phenol

HRID 2236427Notes

Reaction equation

HRID 2236427 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([C:6]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][C:7]=2[C:8]#[N:9])=[CH:2]1>CCO.[Ni]>[NH2:9][CH2:8][C:7]1[CH:10]=[C:11]([OH:14])[CH:12]=[CH:13][C:6]=1[C:3]1[CH:4]=[CH:5][O:1][CH:2]=1

Participants

4

Reactant 1

HCID 593001112-Furan-3-yl-5-hydroxy-benzonitrile

Product 1

HCID 593002373-Aminomethyl-4-furan-3-yl-phenolYield 72%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

The 2-Furan-3-yl-5-hydroxy-benzonitrile obtained above is dissolved in EtOH and to which Raney Ni (1 g of suspension in water) is added. The mixture is then subjected to hydrogenation under H2 (50 psi) for 24 hours. After which Raney Ni is filtered off from celite and EtOH is removed to provide the title compound (40 mg, 72% for two steps). MS (ESI): 190 (M+1)+1, 173 (M+1-NH3)+1.

Workup

  1. additionis added
  2. filtrationAfter which Raney Ni is filtered off from celite and EtOH
  3. customis removed

Sources & evidence

ORD record
ord-5d8dbbbb82024049b6a36d5dd8dfd73f
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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