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

HRID 1818722

反応式

HRID 1818722 の反応式
OC1C=CC=C2C([NH:7]C(=O)C=12)=O.C[O:14][C:15]([C:17]1[C:30]2[C:29](=O)[C:28]3[C:23](=[CH:24][CH:25]=C(CBr)[CH:27]=3)[O:22][C:21]=2[CH:20]=[CH:19][CH:18]=1)=O.[NH2:34][NH2:35].[CH2:36]([OH:38])[CH3:37]>CN(C=O)C>[NH2:7][O:38][CH2:36][C:37]1[CH:25]=[CH:24][C:23]2[O:22][C:21]3[C:30]4=[C:17]([C:15](=[O:14])[NH:34][N:35]=[C:29]4[C:28]=2[CH:27]=1)[CH:18]=[CH:19][CH:20]=3

参加物

6

反応物 4

HCID 702EthanolHCID 9321HydrazineHCID 3460024-hydroxy-2,3-dihydro-1H-isoindole-1,3-dioneHCID 21304612methyl 7-(bromomethyl)-9-oxo-9H-xanthene-1-carboxylate

生成物 1

HCID 1144888510-Aminooxymethyl-2H-7-oxa-1,2-diaza-benzo[de]anthracen-3-one収率 85%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of hydroxy phthalimide (3.6 mmol) in anhydrous DMF was added sodium anhydride 60% in mineral oil (3.6 mmol). The solution was stirred for 20 minutes at room temperature. To this solution was added compound 41 (3.0 mmol). The reaction mixture was stirred at room temperature for two hours and the solvent was removed in vacuo. To the residue was added 100 mL of ethyl acetate. The organic layer was washed with water and brine, then dried over MgSO4. Ethyl acetate was removed in vacuo. A white solid was afforded in 70% 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 down 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 56 in 85% yield. MS (ES+): 282; Mp: 294-296° C.; 1H-NMR (DMSO-d6, 400 MHz): 12.64 (s, 1H), 8.04 (d, J=2.0 Hz, 1H), 7.92-7.86 (m, 2H), 7.73 (dd, J=7.5 and 2.0 Hz, 1H), 7.50 (dd, J=8.5 and 2.0 Hz, 1H), 7.41 (d, J=8.5 Hz, 1H), 4.64 (s, 2H); MS: (ES+): 282; Anal. Calcd. for C15H11N3O3: C, 64.05; H, 3.94; N, 14.94. Found: C, 64.24; H, 4.00; N, 14.97.

後処理

  1. stirringThe reaction mixture was stirred at room temperature for two hours
  2. customthe solvent was removed 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 over MgSO4
  6. customEthyl acetate was removed in vacuo
  7. customA white solid was afforded in 70% yield
  8. stirringThe mixture was stirred for 2 hours
  9. temperatureunder reflux
  10. concentrationThe solution was concentrated down 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

出典と根拠

ORDレコード
ord-1fdbc606b4ad4e4696a830d9faf9a211
出典データセット
uspto-grants-2009_10
特許番号
US07601719B2

関連ノート

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