| Identification | More | [Name]
4-Hydroxy-6,7-dimethoxyqunioline | [CAS]
13425-93-9 | [Synonyms]
4-HYDROXY-6,7-DIMETHOXYQUINOLINE
6,7-DIMETHOXYQUINOLIN-4(1H)-ONE
4-HYDROXY-6,7-DIMETHOXYQUNIOLINE
6,7-Dimethoxy-quinolin-4-ol | [EINECS(EC#)]
811-007-0 | [Molecular Formula]
C11H11NO3 | [MDL Number]
MFCD07368026 | [Molecular Weight]
205.21 | [MOL File]
13425-93-9.mol |
| Chemical Properties | Back Directory | [Melting point ]
227.0 to 231.0 °C | [Boiling point ]
370.9±37.0 °C(Predicted) | [density ]
1.257±0.06 g/cm3(Predicted) | [storage temp. ]
Inert atmosphere,Room Temperature | [solubility ]
DMSO (Slightly), Methanol (Slightly, Sonicated) | [form ]
powder to crystal | [pka]
4.26±0.40(Predicted) | [color ]
Light orange to Yellow to Green | [InChI]
InChI=1S/C11H11NO3/c1-14-10-5-7-8(6-11(10)15-2)12-4-3-9(7)13/h3-6H,1-2H3,(H,12,13) | [InChIKey]
QOGPNCUTXVZQSL-UHFFFAOYSA-N | [SMILES]
N1C2C(=CC(OC)=C(OC)C=2)C(O)=CC=1 | [CAS DataBase Reference]
13425-93-9(CAS DataBase Reference) |
| Hazard Information | Back Directory | [Uses]
6,7-Dimethoxy-4-quinolinol was used in the study of synthesis of ring-substituted 4-aminoquinolines and evaluation fo their antimalarial activities. | [Synthesis]
General procedure for the synthesis of 4-hydroxy-6,7-dimethoxyquinoline-3-carboxylic acid from ethyl 4-hydroxy-6,7-dimethoxyquinoline-3-carboxylate: ethyl 4-hydroxy-6,7-dimethoxyquinoline-3-carboxylate (700 mg, 2.53 mmol) was added to potassium hydroxide (450 mg, 7.6 mmol) dissolved in 20 mL of H2O/EtOH (1:1, v /v) solution. The mixture was placed in a sealed container (XP-500 Plus container) and heated using microwaves (MARS 5 Microwave System) at 180°C, 260-280 psi pressure for 50 min. Upon completion of the reaction, the mixture was cooled to room temperature and transferred to a flask. Subsequently, the solution was acidified to pH about 6 with acetic acid (about 2 mL), saturated with sodium chloride, and extracted with tetrahydrofuran (3 x 100 mL). The organic layers were combined, washed with brine and concentrated to give 6,7-dimethoxyquinolin-4-ol in 90% yield.1H NMR (400 MHz, DMSO-d6) δ ppm: 3.81 (s, 3H), 3.84 (s, 3H), 5.93 (d, J=7.3 Hz, 1H), 7.05 (s, 1H), 7.42 (s, 1H), and 7.76 (d, J=7.3 Hz, 1H). | [storage]
Store at room temperature. | [References]
[1] Patent: WO2005/121125, 2005, A1. Location in patent: Page/Page column 41-42
[2] Journal of the American Chemical Society, 1946, vol. 68, p. 1264 |
|
|