2-[4-(Hydroxymethyl)phenyl]-3-phenyl-1,7-naphthyridin-8(7H)-one → HCID 59846152, compound

HRID 605008Notes

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[CH:15]=[CH:14][NH:13][C:12](=[O:25])[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:12]1[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:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)=[CH:17][C:16]=2[CH:15]=[CH:14][NH:13]1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 2-[4-(hydroxymethyl)phenyl]-3-phenyl-1,7-naphthyridin-8(7H)-one (46 mg, 0.14 mmol) in chloroform (4 mL) and acetonitrile (4 mL) was added activated manganese dioxide (200 mg, 2.2 mmol). This suspension was warmed at 60° C. for three hours. The warm suspension was filtered, rinsed with chloroform and the solvents removed in vacuo to give the title compound. 1H-NMR (500 MHz, CDCl3): δ 12.68 (1H, s), 10.00 (1H, br s), 7.99 (1H, s), 7.82 (2H, d, J=8.3 Hz), 7.77 (2H, d, J=8.3 Hz), 7.40 (1H, d, J=6.9 Hz), 7.31-7.37 (3H, m), 7.20-7.24 (2H, m), 6.61 (1H, d, J=7.1 Hz). m/e (m+1): 327.2.

Workup

filtrationThe warm suspension was filtered
washrinsed with chloroform
customthe solvents removed in vacuo

Sources & evidence

ORD record: ord-1fb8343042c04fbe9cf5cd6b99382a9a
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07910561B2

Reaction notes

Loading…