Sodium ethoxide → 6-Ethoxy-1,7-naphthyridin-8-amine

HRID 1881761Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1881761
[C:1]([CH2:3][C:4]1[C:5]([C:10]#[N:11])=[N:6][CH:7]=[CH:8][CH:9]=1)#[N:2].[O-:12][CH2:13][CH3:14].[Na+]>C(O)C>[CH2:13]([O:12][C:1]1[CH:3]=[C:4]2[C:5](=[C:10]([NH2:11])[N:2]=1)[N:6]=[CH:7][CH:8]=[CH:9]2)[CH3:14]

Komponenten

4

Edukt 2

HCID 2723922Sodium ethoxideHCID 46725983-(Cyanomethyl)pyridine-2-carbonitrile

Produkt 1

HCID 130013416-Ethoxy-1,7-naphthyridin-8-amineAusbeute 14 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a 1 L round bottom flask was added 3-(cyanomethyl)picolinonitrile (3.56 g, 24.9 mmol), absolute ethanol (400 mL), followed by sodium ethoxide (11.1 mL, 21% solution w/v, 29.9 mmol). The mixture was stirred at reflux for 3 h. The solvent was then concentrated and the resultant residue was dissolved in ethyl acetate (200 mL), washed with brine, dried over Na2SO4 and concentrated. The residue was purified by silica gel to yield 6-ethoxy-1,7-naphthyridin-8-amine as a pale yellow solid (0.66 g, 3.49 mmol, 14%). 1H NMR (400 MHz, CDCl3): δ ppm 8.53 (dd, J=3.95, 1.76 Hz, 1H), 7.83 (dd, J=8.35, 1.76 Hz, 1H), 7.39 (dd, J=8.35, 4.39 Hz, 1H), 6.15 (s, 1H), 5.87 (br. s., 2H), 4.22 (q, J=7.03 Hz, 2H), 1.45 (t, J=7.03 Hz, 3H). LC/MS m/z 190 [M+H].

Aufarbeitung

  1. temperatureat reflux for 3 h
  2. concentrationThe solvent was then concentrated
  3. dissolutionthe resultant residue was dissolved in ethyl acetate (200 mL)
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel

Quellen und Nachweise

ORD-Eintrag
ord-4ecf20ef6a21421da66006594979d4be
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08318941B2

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