Benzofuran-3-acetonitrile → 2-Benzo[b]furan-3-ylethylamine

HRID 1762971Notes

Reaction equation

HRID 1762971 reaction equation
[C:1]([CH2:3][C:4]1[C:5]2[CH:12]=[CH:11][CH:10]=[CH:9][C:6]=2[O:7][CH:8]=1)#[N:2].[H][H]>CO.[Ni]>[O:7]1[CH:8]=[C:4]([CH2:3][CH2:1][NH2:2])[C:5]2[CH:12]=[CH:11][CH:10]=[CH:9][C:6]1=2

Participants

5

Reactant 2

HCID 2769401Benzofuran-3-acetonitrileHCID 178418361HCID 178418361, compound

Product 1

HCID 124208122-Benzo[b]furan-3-ylethylamineYield 71%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

To a solution of 3.1 g of 3-cyanomethylbenzo[b]furan in 40 mL of methanol was added 2.4 g of Raney nickel. The reaction was agitated at 25° C. in a Parr apparatus under 40 psi hydrogen for 21/2 hours. The suspension was filtered through a pad of filter aid and the filtrate was evaporated to give 2.2 g (71% yield) of oily product.

Workup

  1. filtrationThe suspension was filtered through a pad of filter aid
  2. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-b1502b6d31d54633b14ae0222507bec2
Source dataset
uspto-grants-1989_05
Patent number
US04835276

Reaction notes

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