Ammonia → 3-(aminomethyl)-4-ethyl-6-methylpyridin-2(1H)-one

HRID 85535Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 85535
[CH2:1]([C:3]1[CH:8]=[C:7]([CH3:9])[NH:6][C:5](=[O:10])[C:4]=1[C:11]#[N:12])[CH3:2].N>[Ni].CO>[NH2:12][CH2:11][C:4]1[C:5](=[O:10])[NH:6][C:7]([CH3:9])=[CH:8][C:3]=1[CH2:1][CH3:2]

Komponenten

5

Edukt 2

HCID 222AmmoniaHCID 156418004-Ethyl-6-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile

Produkt 1

HCID 674665833-(aminomethyl)-4-ethyl-6-methylpyridin-2(1H)-oneAusbeute 54,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 935NickelKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

To a suspension of Raney Nickel (6 g) in methanol (200 mL) was added 4-ethyl-1,2-dihydro-6-methyl-2-oxopyridine-3-carbonitrile (10 g, 61.7 mmol) and methanolic ammonia (750 mL). The reaction mixture was stirred at room temperature under hydrogen pressure (80 psi) for 48 hrs. The reaction mixture was filtered through Celite and washed with methanol (250 mL). The filtrate was concentrated under reduced pressure and the residue purified by filter column using silica gel (60-120 mesh), eluted with 10% MeOH in CHCl3, to afford 3-(amino methyl)-4-ethyl-6-methylpyridin-2(1H)-one (5.6 g, 54%) as an off white solid. 1H NMR (DMSO-D6, 400 MHz) (free amine): δ ppm 1.063-1.101 (t, 3H, J=7.6 Hz), 2.101 (s, 3H), 2.412-2.449 (m, 2H), 3.448 (s, 2H), 5.835 (s, 1H). MS(ES) [M+H]+ 167.06.

Aufarbeitung

  1. filtrationThe reaction mixture was filtered through Celite
  2. washwashed with methanol (250 mL)
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customthe residue purified
  5. filtrationby filter column
  6. washeluted with 10% MeOH in CHCl3

Quellen und Nachweise

ORD-Eintrag
ord-1a0c37bbf97a4379b0cf2ef9e7f0ebae
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846935B2

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