(E)-3-(7-Fluoro-benzofuran-4-yl)-acrylonitrile → 3-(7-Fluoro-2,3-dihydro-benzofuran-4-yl)-propylamine

HRID 1602396Notes

Reaction equation

HRID 1602396 reaction equation
[F: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)C.N.[Pd].[Rh]>[F:1][C:2]1[C:10]2[O:9][CH2:8][CH2:7][C:6]=2[C:5]([CH2:11][CH2:12][CH2:13][NH2:14])=[CH:4][CH:3]=1

Participants

6

Reactant 1

HCID 19611668(E)-3-(7-Fluoro-benzofuran-4-yl)-acrylonitrile

Product 1

HCID 196116493-(7-Fluoro-2,3-dihydro-benzofuran-4-yl)-propylamineYield 98.2%

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 23948RhodiumCatalystHCID 222AmmoniaSolventHCID 702EthanolSolvent

Procedure

A solution of (E)-3-(7-fluoro-benzofuran-4-yl)-acrylonitrile (0.25 g) in ethanol (25 ml), ammonia (0.88; 10 ml) containing 10% palladium on charcoal (50 mg; 50% wet paste) and 5% rhodium on charcoal (50 mg) was hydrogenated at 70 psi and 70° for 18 h. The solution was filtered through hyflo and evaporated to dryness and the residue purified by column chromatography. Eluting with dichloromethane/ethanol/ammonia 100:8:1 gave the title compound (256 mg).

Workup

  1. filtrationThe solution was filtered through hyflo
  2. customevaporated to dryness
  3. customthe residue purified by column chromatography
  4. washEluting with dichloromethane/ethanol/ammonia 100:8:1

Sources & evidence

ORD record
ord-9d4aed45b11b437094c2ccbd8da1da85
Source dataset
uspto-grants-1999_11
Patent number
US05981572

Reaction notes

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