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 604998Notes

Reaction equation

[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

Participants

Conditions

Temperature: 60 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-51bf0a469c43421b860874b224cdd36a
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07910561B2

Reaction notes

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