1-[1,8]Naphthyridin-4-yl-ethanol → 1-[1,8]Naphthyridin-4-ylethanone

HRID 2374145Notes

Reaction equation

[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][N:9]=2)[C:4]([CH:11]([OH:13])[CH3:12])=[CH:3][CH:2]=1>CCOC(C)=O>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][N:9]=2)[C:4]([C:11](=[O:13])[CH3:12])=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 80 °C

Procedure

1-[1,8]Naphthyridin-4-yl-ethanol (1.44 g, 8.26 mmol) was dissolved in EtOAc (250 mL), treated with IBX (7.8 g, 24.8 mmol) and heated to 80° C. for 6 h. The solution was cooled to RT and the solids removed by filtration. The product was purified (SGC using MeCN eluant) yielding the title compound (1.22 g). MS (ESI+) for m/z 173 (M+H)+. 1H NMR (CDCl3) δ 9.13 (d, 1H), 9.03 (dd, 1H), 8.85 (dd, 1H), 7.70 (d, 1H), 7.46 (dd, 1H), 2.64 (s, 3H).

Workup

additiontreated with IBX (7.8 g, 24.8 mmol)
temperatureThe solution was cooled to RT
customthe solids removed by filtration
customThe product was purified (SGC using MeCN eluant)

Sources & evidence

ORD record: ord-1c344b912d2048a8a55aa2777c4c059a
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07462600B2

Reaction notes

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