(E)-(6-methoxy-2-phenylindan-1-ylidene)acetonitrile → 2-(6-Methoxy-2-phenylindan-1-ylidene)ethylamine

HRID 582195Notes

Reaction equation

HRID 582195 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][CH:8]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)/[C:9]/2=[CH:12]\[C:13]#[N:14])=[CH:5][CH:4]=1.N.C(O)C>C(O)C.[Co]>[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][CH:8]([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:9]2=[CH:12][CH2:13][NH2:14])=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 10858248(E)-(6-methoxy-2-phenylindan-1-ylidene)acetonitrileHCID 22020343Ethanol, reaction products with ammonia, distn. residues

Product 1

HCID 570553732-(6-Methoxy-2-phenylindan-1-ylidene)ethylamine

Reagents, catalysts & solvents 2

HCID 104730CobaltCatalystHCID 702EthanolSolvent

Procedure

To a solution of (E)-(6-methoxy-2-phenylindan-1-ylidene)acetonitrile (0.45 g, 1.72 mmol.) in ethanol (30 ml) were added a saturated ammonia/ethanol solution (10 ml) and Raney cobalt (0.3 g). The mixture was stirred for 10 hours at 10 hours at room temperature under hydrogen atmosphere (5 kgf/cm2). The Raney cobalt was filtered off, then the solvent was filtered off under reduced pressure to leave 2-(6-methoxy-2-phenylindan-1-ylidene)ethylamine., which was dissolved in a hydrogen chloride/ethanol solution. The solvent was then distilled off under reduced pressure to afford the titled compound (0.3 g, yield 58%). This compound was used for the subsequent reaction without further purification.

Workup

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

Sources & evidence

ORD record
ord-d11e4db540cc4e86aeae124281e2527a
Source dataset
uspto-grants-1999_07
Patent number
US05922771

Reaction notes

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