2-[4-(hydroxymethyl)phenyl]-3-phenyl-1,6-naphthyridin-5(6H)-one → 4-(5-Oxo-3-phenyl-5,6-dihydro-1,6-naphthyridin-2-yl)benzaldehyde

HRID 604998Notizen

Reaktionsgleichung

[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:18]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:17][C:16]3[C:15](=[O:25])[NH:14][CH:13]=[CH:12][C:11]=3[N:10]=2)=[CH:5][CH:4]=1>C(Cl)(Cl)Cl.C(#N)C.[O-2].[O-2].[Mn+4]>[O:25]=[C:15]1[NH:14][CH:13]=[CH:12][C:11]2[N:10]=[C:9]([C:6]3[CH:7]=[CH:8][C:3]([CH:2]=[O:1])=[CH:4][CH:5]=3)[C:18]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:17][C:16]1=2

Komponenten

Reaktionsbedingungen

Temperatur: 60 °C

Versuchsvorschrift

To a solution of 2-[4-(hydroxymethyl)phenyl]-3-phenyl-1,6-naphthyridin-5(6H)-one (316 mg, 0.96 mmol) in chloroform (15 mL) and acetonitrile (15 mL) was added activated manganese dioxide (903 mg, 10 mmol) which was warmed at 60° C. for three hours. The warm suspension was filtered, rinsed with chloroform and the solvents removed in vacuo. The residue was triturated with diethyl ether and the suspension filtered to give the title compound as a pinkish solid. 1H-NMR (500 MHz, CDCl3): δ 10.20 (1H, s), 9.89 (1H, br s), 8.73 (1H, s), 7.81 (2H, d, J=8 Hz), 7.61 (2H, d, J=8 Hz), 7.35-7.38 (1H, m), 7.30-7.32 (2H, m), 7.21-7.22 (2H, m), 6.91 (1H, d, J=7.3 Hz). m/e (m+1): 327.2.

Aufarbeitung

filtrationThe warm suspension was filtered
washrinsed with chloroform
customthe solvents removed in vacuo
customThe residue was triturated with diethyl ether
filtrationthe suspension filtered

Quellen und Nachweise

ORD-Eintrag: ord-51bf0a469c43421b860874b224cdd36a
Quelldatensatz: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07910561B2

Notizen zur Reaktion

Wird geladen…