7-Methoxy-1,8-naphthyridin-2(1H)-one synthesis

7synthesis methods

Product Name:7-Methoxy-1,8-naphthyridin-2(1H)-one
CAS Number:106582-47-2
Molecular formula:C9H8N2O2
Molecular Weight:176.17

15944-34-0
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106582-47-2
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Yield:106582-47-2 100%

Reaction Conditions:

with sodium methylate in methanol; for 15 h;Reflux;

Steps:

B

To a solution of 7-chloro-lH-[l,8]naphthyridin-2-one (prepared as described in J. Org. Chem. (1990), 55, 4744; 5.36 g, 29.68 mmol) in MeOH (98 niL) was added NaOMe (25 wt% in MeOH, 161 rnL). The resulting solution was stirred at reflux for 15 h. The solvent was removed in vacuo. Water (100 mL) and EA (80 mL) were added. The phases were separated and the aq. layer was extracted with EA (8 x 80 mL). The combined org. layers were washed with brine (50 mL), dried over MgSO₄, filtered and evaporated under reduced pressure. The title compound was obtained as a beige solid (5.22 g, 100% yield). ¹H NMR (d₆DMSO) δ: 11.96 (s, 1Η); 7.96 (d, J = 8.5 Hz, IH); 7.81 (d, J = 9.4 Hz, IH); 6.63 (d, J = 8.5 Hz, IH); 6.34 (d, J = 9.4 Hz, IH); 3.90 (s, 3H).

References:

WO2010/116337,2010,A1 Location in patent:Page/Page column 32

124-41-4 Synthesis