1,2,6,7-tetrahydro-8H-indeno-(5,4-B)-furan-8-ylidene acetonitrile → Ethanamine, 2-(1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-ylidene)-

HRID 324638Notes

Reaction equation

HRID 324638 reaction equation
N.C(O)C.[CH2:5]1[CH2:9][O:8][C:7]2[CH:10]=[CH:11][C:12]3[CH2:13][CH2:14]/[C:15](=[CH:17]\[C:18]#[N:19])/[C:16]=3[C:6]1=2.[H][H]>[Co].C(O)C>[CH2:5]1[CH2:9][O:8][C:7]2[CH:10]=[CH:11][C:12]3[CH2:13][CH2:14][C:15](=[CH:17][CH2:18][NH2:19])[C:16]=3[C:6]1=2

Participants

6

Reactant 3

HCID 118303811,2,6,7-tetrahydro-8H-indeno-(5,4-B)-furan-8-ylidene acetonitrileHCID 22020343Ethanol, reaction products with ammonia, distn. residuesHCID 178418361HCID 178418361, compound

Product 1

HCID 54293176Ethanamine, 2-(1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-ylidene)-

Reagents, catalysts & solvents 2

HCID 104730CobaltCatalystHCID 702EthanolSolvent

Procedure

A saturated ammonia/ethanol solution (150 ml) and Raney cobalt (8.4 g) were added to an ethanol (150 ml) solution of (E)-(1,6,7,8-tetrahydro-2H-indeno[5,4-b]-furan-8-ylidene)acetonitrile (2.6 g, 13.2 mmol), and the reaction mixture was stirred at room temperature in a hydrogen atmosphere (5 kgf/cm2) for 3 hours. The Raney cobalt was filtered off and the solvent was distilled off under reduced pressure to give 2-(1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-ylidene)ethylamine. To this residue was added a saturated hydrogen chloride/ethanol solution (100 ml), followed by 1 hour of heating under reflux. The reaction solution was concentrated and the residue obtained was recrystallized from ethanol to give 2.75 g (yield: 88%) of the target compound.

Workup

  1. filtrationThe Raney cobalt was filtered off
  2. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-e5ec8fbf47e84c1dafab3dc493f4db1d
Source dataset
uspto-grants-2001_04
Patent number
US06218429B1

Reaction notes

Loading…