Ethanol, reaction products with ammonia, distn. residues → (E)-1-(2-Aminoethylidene)-6-methoxyindan

HRID 1977991Notes

Reaction equation

HRID 1977991 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]>[NH2:14][CH2:13]/[CH:12]=[C:9]1\[CH2:8][CH2:7][C:6]2[C:10]\1=[CH:11][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2

Participants

5

Reactant 2

HCID 22020343Ethanol, reaction products with ammonia, distn. residuesHCID 53954914(6-Methoxyindan-1-ylidene) acetonitrile

Product 1

HCID 10987044(E)-1-(2-Aminoethylidene)-6-methoxyindanYield 86%

Reagents, catalysts & solvents 2

HCID 104730CobaltCatalystHCID 702EthanolSolvent

Procedure

To a solution of (6-methoxyindan-1-ylidene) acetonitrile (1.60 g, 8.64 mmol) in ethanol (80 ml) were added a 2M ammonia/ethanol solution (40 ml) and Raney cobalt (1.6 g). The mixture was stirred, under hydrogen atmosphere (4 kgf/cm2), for 32 hours at 40° C., and for further 8 hours at 70° C. The Raney cobalt was filtered off, then the solvent was distilled off under reduced pressure. The residue was purified by means of a silica gel column chromatography (chloroform:methanol=9:1 to chloroform:methanol:triethylamine=90:8:2) to give the above-titled compound (yield 1.40 g, 86%, oily).

Workup

  1. waitfor further 8 hours at 70° C
  2. filtrationThe Raney cobalt was filtered off
  3. distillationthe solvent was distilled off under reduced pressure
  4. customThe residue was purified by means of a silica gel column chromatography (chloroform:methanol=9:1 to chloroform:methanol:triethylamine=90:8:2)

Sources & evidence

ORD record
ord-34cb841497864788b307d63b51f391d7
Source dataset
uspto-grants-2001_05
Patent number
US06235789B1

Reaction notes

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