Diethyl phenylmalonate → 4-Hydroxy-6-oxo-2-(4-phenoxyphenyl)-5-phenyl-1,6-dihydropyridine-3-carbonitrile

HRID 81054

Reaktionsgleichung

Reaktionsgleichung von HRID 81054
[NH2:1]/[C:2](/[C:6]1[CH:11]=[CH:10][C:9]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:8][CH:7]=1)=[CH:3]\[C:4]#[N:5].[C:19]1([CH:25]([C:31](OCC)=[O:32])[C:26](OCC)=[O:27])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>>[OH:32][C:31]1[C:3]([C:4]#[N:5])=[C:2]([C:6]2[CH:11]=[CH:10][C:9]([O:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:8][CH:7]=2)[NH:1][C:26](=[O:27])[C:25]=1[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Komponenten

3

Edukt 2

HCID 66514Diethyl phenylmalonateHCID 66927049(Z)-3-amino-3-(4-phenoxyphenyl)acrylonitrile

Produkt 1

HCID 696702244-Hydroxy-6-oxo-2-(4-phenoxyphenyl)-5-phenyl-1,6-dihydropyridine-3-carbonitrileAusbeute 62 %

Versuchsvorschrift

A mixture of (Z)-3-amino-3-(4-phenoxyphenyl)acrylonitrile (717 mg, 3.03 mmol) in diethyl 2-phenylmalonate (8 mL, 37.1 mmol) was microwaved at 250° C. for 15 min. After cooling to room temperature, the resulting suspension was filtered. The solid was washed with 20% isopropyl alcohol in heptanes and dried under vacuum to give 4-hydroxy-6-oxo-2-(4-phenoxyphenyl)-5-phenyl-1,6-dihydropyridine-3-carbonitrile (714 mg, 62% yield). 1H NMR (500 MHz, DMSO-d6) δ ppm 12.23 (1H, br. s), 10.76 (1H, br. s), 7.72 (2H, δ, J=8.80 Hz), 7.46-7.51 (2H, m), 7.39-7.44 (2H, m), 7.30-7.36 (3H, m), 7.26 (1H, t, J=7.42 Hz), 7.15 (2H, δ, J=7.70 Hz), 7.10 (2H, δ, J=8.80 Hz); MS (ES+) m/z: 381 (M+H); LC retention time: 3.820 min (analytical HPLC Method A).

Aufarbeitung

  1. customwas microwaved at 250° C. for 15 min
  2. filtrationthe resulting suspension was filtered
  3. washThe solid was washed with 20% isopropyl alcohol in heptanes
  4. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-8f85c58d571b49c5bc609895aeb7cc6d
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846673B2

Verknüpfte Notizen

Wird geladen…