Water → 1,5-Naphthyridine-1(2H)-acetaldehyde, 7-fluoro-2-oxo-

HRID 656869Notes

Reaction equation

[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8](=[O:15])[N:9]2[CH2:12][CH:13]=C)=[N:4][CH:3]=1.O.I([O-])(=O)(=O)=[O:18].[Na+]>O1CCOCC1.[Os](=O)(=O)(=O)=O>[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8](=[O:15])[N:9]2[CH2:12][CH:13]=[O:18])=[N:4][CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

7-Fluoro-1-(2-propen-1-yl)-1,5-naphthyridin-2(1H)-one (1.683 g, 8.25 mmol) was dissolved in 1,4-dioxane (100 ml) and water (50 ml) was added. The solution was cooled to 0° C. and sodium periodate (5.29 g, 24.75 mmol) was added, followed by osmium tetroxide (9 mL of 4% aqueous solution). The stirred mixture was allowed to warm to rt, then stirred at rt for 1 h. The mixture was then treated with a further 100 ml of water and sodium periodate (10.58 g, 49.5 mmol) and stirred at rt for 1 h. The mixture was evaporated to approximately 50 ml and the residue was extracted with 20% methanol in DCM (3×300 ml). The organic extracts were combined, dried over anhydrous magnesium sulphate, filtered and evaporated to give (7-fluoro-2-oxo-1,5-naphthyridin-1(2H)-yl)acetaldehyde (mainly as the methyl hemiacetal) as an off-white solid (1.531 g, 90%).

Workup

temperatureto warm to rt
stirringstirred at rt for 1 h
customThe mixture was evaporated to approximately 50 ml
extractionthe residue was extracted with 20% methanol in DCM (3×300 ml)
dry with materialdried over anhydrous magnesium sulphate
filtrationfiltered
customevaporated

Sources & evidence

ORD record: ord-ea648da393d848d3baf06fef1b1f16d9
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08071592B2

Reaction notes

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