Ammonia → 2-Anthracen-9-yl-ethylamine

HRID 910711

Reaktionsgleichung

Reaktionsgleichung von HRID 910711
[CH:1]1[C:14]2[C:5](=[CH:6][C:7]3[C:12]([C:13]=2[CH2:15][C:16]#[N:17])=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:4]=[CH:3][CH:2]=1.[NH4+].[OH-].N>C(O)C.[Ni]>[CH:11]1[C:12]2[C:7](=[CH:6][C:5]3[C:14]([C:13]=2[CH2:15][CH2:16][NH2:17])=[CH:1][CH:2]=[CH:3][CH:4]=3)[CH:8]=[CH:9][CH:10]=1

Komponenten

6

Edukt 3

HCID 222AmmoniaHCID 14923Ammonium HydroxideHCID 3156629-Anthraceneacetonitrile

Produkt 1

HCID 543274372-Anthracen-9-yl-ethylamineAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 935NickelKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of anthracen-9-yl-acetonitrile (3.0 g, 13.82 mmol) in ethanol (150 mL) was added concentrated NH4OH (15 mL) and Raney nickel (15 g), and ammonia gas was bubbled through the mixture at 0° C. for 10 minutes. The suspension was hydrogenated for 48 hours at room temperature. Air was bubbled through the solution and Raney nickel was removed by filtration. The filtrate was concentrated and the oily residue was dissolved in CH2Cl2, washed with an aqueous solution of sodium carbonate (Na2CO3, 10%), dried over MgSO4 and concentrated. The resulting solid was purified by recrystallization from a mixture of hexane and CH2Cl2 (7:3) to give 2-anthracen-9-yl-ethylamine as yellow crystals (2.60 g, 85%). 1H NMR (CDCl3) δ 8.37 (1H, s), 8.33 (2H, d), 8.02 (2H, d), 7.54-7.47 (4H, m), 3.86 (2H, t), 3.19 (2H, t), 1.34 (2H, br-s).

Aufarbeitung

  1. customwas bubbled through the mixture at 0° C. for 10 minutes
  2. customAir was bubbled through the solution and Raney nickel
  3. customwas removed by filtration
  4. concentrationThe filtrate was concentrated
  5. dissolutionthe oily residue was dissolved in CH2Cl2
  6. washwashed with an aqueous solution of sodium carbonate (Na2CO3, 10%)
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated
  9. customThe resulting solid was purified by recrystallization from a mixture of hexane and CH2Cl2 (7:3)

Quellen und Nachweise

ORD-Eintrag
ord-181fe1c4deff4b2caefc14831f34ef0e
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08022214B2

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