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CAS No. : | 13207-66-4 | MDL No. : | MFCD00185837 |
Formula : | C9H8N2O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | YDEUKNRKEYICTH-UHFFFAOYSA-N |
M.W : | 160.17 | Pubchem ID : | 416002 |
Synonyms : |
5A8HQ
|
Chemical Name : | 5-Aminoquinolin-8-ol |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H332-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | With sodium dichromate; sulfuric acid In dichloromethane; water at 0℃; for 1 h; | To 0.80g (5.0mmol) of 5-amino-8-hydroxyquinoline in 150mL of CH2Cl2 at 0°C was added 150mL of a 5percent aqueous solution of H2SO4 followed by slow addition of a pre-cooled solution of 2.98g (10.0mmol) of sodium dichromate in 50mL of H2O at 0°C. The yellow solution became orange and biphasic. After 1h, the reaction was extracted with methylene chloride and washed with brine. The organic extract was dried over magnesium sulfate and filtered. The solvent was removed under reduced pressure to give a yellow solid. The solid was purified using silica gel column chromatography eluting 3:2 ethyl acetate–hexanes to afford 0.49g (61percent) of quinoline-5,8-dione. 1H NMR (400MHz, CDCl3) δ: 8.90 (d, J=4.6Hz, 1H), 8.71 (s, 1H), 8.41 (d, J=8.1Hz, 1H), 7.74 (dd, J=4.6, 8.1Hz, 1H), 7.06 (d, J=10.9Hz, 1H), 6.90 (d, J=10.9Hz, 1H). 13C NMR (100.17MHz, CDCl3) δ: 182.1, 180.7, 148.8, 147.2, 138.2, 138.1, 135.4, 129.0, 128.3. |