Sodium Hydroxide → Bis(2-pyridyl)methylamine

HRID 1946624

Reaktionsgleichung

Reaktionsgleichung von HRID 1946624
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1)=[N:8]O.C([O-])(=O)C.[NH4+].[OH-].[Na+]>C(O)C.[Zn]>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1)[NH2:8]

Komponenten

6

Edukt 3

HCID 14798Sodium HydroxideHCID 73805Di-2-pyridinylmethanone oximeHCID 517165Ammonium Acetate

Produkt 1

HCID 11106041Bis(2-pyridyl)methylamineAusbeute 61 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23994ZincKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

Dipyridin-2-ylmethanone oxime (500 mg, 2.510 mmol) and ammonium acetate were solubilized in ethanol and the mixture was reflux for 3 hours adding portion of zinc at 0 h, 1 h and 2 h. The reaction mixture was cooled down to room temperature and stirred over night. The pH was adjusted to 12 with sodium hydroxide and the mixture was filtered through celite. The mixture was diluted with ethyl acetate and the organic layer was washed with brine, dried over magnesium sulfate, filtered and evaporated to afford title compound 405 (282 mg, 61%) as a light yellow oil. MS (m/z): 186.2 (M+H). 1H NMR (CDCl3) δ (ppm): 8.50-8.49 (m, 2H), 7.56 (td, J=7.7, 1.8 Hz, 2H), 7.33 (dt, J=8.0, 0.9 Hz, 2H), 7.08 (ddd, J=7.4, 4.9, 1.2 Hz, 2H), 5.26 (s, 1H), 2.38 (s, 2H).

Aufarbeitung

  1. temperaturethe mixture was reflux for 3 hours
  2. custom1 h and 2 h
  3. filtrationthe mixture was filtered through celite
  4. additionThe mixture was diluted with ethyl acetate
  5. washthe organic layer was washed with brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-f8ff07573247488285ac5a27ceb1831f
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08399452B2

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