(E)-(6-methoxyindan-1-ylidene)acetonitrile → (E)-1-(2-Aminoethylidene)-6-methoxyindan

HRID 324618Notes

Reaction equation

HRID 324618 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][CH2:8]/[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][CH2:8]/[C:9]/2=[CH:12]\[CH2:13][NH2:14])=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 11830118(E)-(6-methoxyindan-1-ylidene)acetonitrileHCID 22020343Ethanol, reaction products with ammonia, distn. residues

Product 1

HCID 10987044(E)-1-(2-Aminoethylidene)-6-methoxyindan

Reagents, catalysts & solvents 2

HCID 104730CobaltCatalystHCID 702EthanolSolvent

Procedure

To a solution of (E)-(6-methoxyindan-1-ylidene) acetonitrile (5.0 g, 27 mmol.) in ethanol (50 mL) were added a saturated ammonia/ethanol solution (250 mL) and Raney cobalt (10 g). The mixture was stirred for 5 hours at room temperature under hydrogen atmosphere (5 kgf/cm2). The Raney cobalt was filtered off, and the solvent was distilled off under reduced pressure to leave (E)-2-(6-methoxyindan-1-ylidene)ethylamine. This oily residue was dissolved in ethanol (20 mL). The solution was cooled to −40° C., to which was added a saturated hydrogen chloride/ethanol solution. The resulting crystalline precipitate was collected by filtration to obtain the title compound (yield 4.3 g, 71%).

Workup

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

Sources & evidence

ORD record
ord-f8eafb4f669640bba8aed99bd9065556
Source dataset
uspto-grants-2001_04
Patent number
US06218429B1

Reaction notes

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