反应详情

温度

110 °C

To a stirred solution of ethyl 2-((2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)oxy)acetate (0.1 g, 0.4 mmol) in dry toluene (2 mL), 2-(4-chlorophenyl)-N′-hydroxyacetimidamide (0.073 g, 0.4 mmol) and potassium carbonate (0.1 g, 8 mmol) were added and heated to 110° C. in a microwave oven for 30 min. Solvent was removed under vacuum. Water (5 mL) was added to the residue, and the solid which formed was filtered, dried, and recrystallized using a mixture of ACN/Ethanol to afford 6-((3-(4-chlorobenzyl)-1,2,4-oxadiazol-5-yl)methoxy)-3,4-dihydroquinolin-2(1H)-one as an off-white solid (40 mg, 27%). 1H NMR: 400 MHZ, DMSO-d6: δ 2.40 (t, J=7.20 Hz, 2H), 2.82 (t, J=7.60 Hz, 2H), 4.14 (s, 2H), 5.39 (s, 2H), 6.78-6.83 (m, 2H), 6.89 (d, J=2.40 Hz, 1H), 7.33 (d, J=8.40 Hz, 2H), 7.40 (d, J=8.40 Hz, 2H), 9.95 (s, 1H). LCMS: RT 1.85 min. LCMS (ES-API), m/z 370.0 (M+H).

1. customSolvent was removed under vacuum
2. additionWater (5 mL) was added to the residue
3. customthe solid which formed
4. filtrationwas filtered
5. customdried
6. customrecrystallized
7. additiona mixture of ACN/Ethanol