Reaktion #47196

ord-f46bacf9bd4f4633ae87241f3c9c8450

Reaktionsgleichung

N#Cc1ccc(N)c2ccccc12
4-aminonaphthalene-1-carbonitrile
B.C1CCOC1
BH3.THF
NCc1ccc(N)c2ccccc12
4-(aminomethyl)naphthalen-1-amine

Reaktionsbedingungen

Temperatur
70°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeThe vial was capped
  2. 2
    TemperaturThe reaction was cooled down to room temperature
  3. 3
    Sonstigequenched by drop wise addition of methanol (2 mL)
  4. 4
    workup.STIRRINGstirred at room temperature for 30 minutes
  5. 5
    Filtrationfiltered
  6. 6
    workup.STIRRINGstirred with Dowex 50WX2-200 resin (1 g) for 26.5 hours
  7. 7
    FiltrationThe resin was filtered
  8. 8
    Waschenwashed with methanol (20 mL) and 10% aqueous ammonia (50 mL)
  9. 9
    SonstigeThe solvent was removed under vacuum
  10. 10
    SonstigeThe material was used without any further purification in the next step

Vorschrift

To a vial containing 4-aminonaphthalene-1-carbonitrile (0.59 mmol) was added BH3.THF (1M solution (1.2 mmol). The vial was capped and stirred at 70° C. for 19.5 hours. The reaction was cooled down to room temperature and quenched by drop wise addition of methanol (2 mL), stirred at room temperature for 30 minutes, filtered and stirred with Dowex 50WX2-200 resin (1 g) for 26.5 hours. The resin was filtered, washed with methanol (20 mL) and 10% aqueous ammonia (50 mL). The solvent was removed under vacuum. The material was used without any further purification in the next step.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07741479B2uspto-grants-2010_06