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

HRID 272575

Reaction equation

HRID 272575 reaction equation
C[O:2][C:3]([C:5]1[C:18]2[C:17](=O)[C:16]3[C:11](=[CH:12][CH:13]=C(CBr)[CH:15]=3)[O:10][C:9]=2[CH:8]=[CH:7][CH:6]=1)=O.[NH2:22][NH2:23].[CH2:24]([OH:26])[CH3:25]>O.CC(C)=O.[N+]([O-])([O-])=O.[Ag+]>[OH:26][CH2:24][C:25]1[CH:13]=[CH:12][C:11]2[O:10][C:9]3[C:18]4=[C:5]([C:3](=[O:2])[NH:22][N:23]=[C:17]4[C:16]=2[CH:15]=1)[CH:6]=[CH:7][CH:8]=3

Participants

7

Reactant 3

HCID 702EthanolHCID 9321HydrazineHCID 21304612methyl 7-(bromomethyl)-9-oxo-9H-xanthene-1-carboxylate

Product 1

HCID 1145979210-Hydroxymethyl-2H-7-oxa-1,2-diaza-benzo[de]anthracen-3-oneYield 95%

Reagents, catalysts & solvents 3

HCID 24470Silver NitrateCatalystHCID 180AcetoneSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-67bc87742c1048cdb85fba0ba37f012f
Source dataset
uspto-grants-2008_11
Patent number
US07456178B2

Linked notes

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