(E)-3-(7-Chloro-benzofuran-4-yl)-acrylonitrile → 3-(2,3-Dihydro-benzofuran-4-yl)-propylamine hydrochloride

HRID 1602382Notes

Reaction equation

HRID 1602382 reaction equation
[Cl:1][C:2]1[C:10]2[O:9][CH:8]=[CH:7][C:6]=2[C:5](/[CH:11]=[CH:12]/[C:13]#[N:14])=[CH:4][CH:3]=1>C(O)(=O)C.[Pd]>[ClH:1].[O:9]1[C:10]2[CH:2]=[CH:3][CH:4]=[C:5]([CH2:11][CH2:12][CH2:13][NH2:14])[C:6]=2[CH2:7][CH2:8]1

Participants

4

Reactant 1

HCID 19611650(E)-3-(7-Chloro-benzofuran-4-yl)-acrylonitrile2×

Product 1

HCID 196116703-(2,3-Dihydro-benzofuran-4-yl)-propylamine hydrochloride

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of the (E)-3-(7-chloro-benzofuran-4-yl)-acrylonitrile (intermediate 3) (1.0 g) in acetic acid (30 ml) containing 10% palladium on charcoal (50 mg; 50% wet paste) and 5% platinium on charcoal (50 mg) was hydrogenated at 100 psi and 50° for 3 days. The solution was filtered through hyflo and evaporated to dryness and the residue recrystallised from isopropanol to give the title compound as white plates (583 mg).

Workup

  1. filtrationThe solution was filtered through hyflo
  2. customevaporated to dryness
  3. customthe residue recrystallised from isopropanol

Sources & evidence

ORD record
ord-6f0510d0d41143988681b54c9514f5c0
Source dataset
uspto-grants-1999_11
Patent number
US05981572

Reaction notes

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