Ethanol → 10-Hydroxymethyl-2H-7-oxa-1,2-diaza-benzo[de]anthracen-3-one

温度

50 °C

To a solution of compound 41 (4.2 mmol) in 20 mL of water and 20 mL of acetone was added silver nitrate (8.4 mmol). The reaction mixture was stirred at 50° C. for 2 hours. Black precipitate was filtered out. The filtrate was concentrated in vacuo. To the residue was added 100 mL of ethyl acetate. The organic layer was washed with water and brine, then dried with MgSO4. Solvents was removed in vacuo to afford a white solid in 86% yield. The white solid was added to a mixture of hydrazine and ethyl alcohol. The mixture was stirred for 2 hours under reflux. The solution was concentrated in vacuo. To the concentrated solution was added water. A white precipitate was formed, filtered out, and washed with extra water. The white solid was collected and dried to give a white solid product 57 in 95% yield. MS (ES+): 267, 1H-NMR (DMSO-d6, 400 MHz): 12.56 (s, 1H), 7.99 (d, J=2.0 Hz, 1H), 7.91-7.81 (m, 2H), 7.63 (dd, J=7.5 and 2.0 Hz, 1H), 7.43 (dd, J=8.5 and 2.0 Hz, 1H), 7.30 (d, J=8.5 Hz, 1H), 4.50 (d, J=6.0 Hz, 2H); Anal. Calcd. for C15H10N2O3.(0.08 hydrazine): C, 67.02; H, 3.87; N, 11.25. Found: C, 67.29; H, 3.82; N, 11.51.

1. filtrationBlack precipitate was filtered out
2. concentrationThe filtrate was concentrated in vacuo
3. additionTo the residue was added 100 mL of ethyl acetate
4. washThe organic layer was washed with water and brine
5. dry with materialdried with MgSO4
6. customSolvents was removed in vacuo
7. customto afford a white solid in 86% yield
8. stirringThe mixture was stirred for 2 hours
9. temperatureunder reflux
10. concentrationThe solution was concentrated in vacuo
11. additionTo the concentrated solution was added water
12. customA white precipitate was formed
13. filtrationfiltered out
14. washwashed with extra water
15. customThe white solid was collected
16. customdried

ORDレコード

ord-67bc87742c1048cdb85fba0ba37f012f

出典データセット

uspto-grants-2008_11

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07456178B2