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CAS No. : | 127285-54-5 | MDL No. : | MFCD09031937 |
Formula : | C11H11NO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | QOGPNCUTXVZQSL-UHFFFAOYSA-N |
M.W : | 205.21 | Pubchem ID : | 459611 |
Synonyms : |
|
Num. heavy atoms : | 15 |
Num. arom. heavy atoms : | 10 |
Fraction Csp3 : | 0.18 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 57.55 |
TPSA : | 51.32 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.49 cm/s |
Log Po/w (iLOGP) : | 1.93 |
Log Po/w (XLOGP3) : | 1.5 |
Log Po/w (WLOGP) : | 1.55 |
Log Po/w (MLOGP) : | 0.24 |
Log Po/w (SILICOS-IT) : | 2.56 |
Consensus Log Po/w : | 1.55 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.42 |
Solubility : | 0.783 mg/ml ; 0.00381 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.19 |
Solubility : | 1.34 mg/ml ; 0.00652 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.87 |
Solubility : | 0.0277 mg/ml ; 0.000135 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.86 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H319 | 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 |
---|---|---|
87.6% | With trichlorophosphate In toluene for 1 h; Heating / reflux | (4) Step of chlorination: Toluene (3 L) and phosphorus oxychloride (1300 g) were added to 6,7-dimethoxy-4-quinolone (1056 g), and the mixture was heated under reflux with stirring for one hr. The reaction solution was neutralized with an aqueous sodium hydroxide solution at 0°C. The resultant precipitate was collected by filtration and was slurried in water (10 L) for washing. The slurry was filtered, and the filtered product was then dried under the reduced pressure to give 4-chloro-6,7-dimethoxyquinoline (928 g, yield 87.6percent). 1H-NMR (400 MHz, DMSO-d6/ppm); δ 3.95 (s, 3H), 3.96 (s, 3H), 7.35 (s, 1H), 7.43 (s, 1H), 7.54 (d, 1H), 8.59 (d, 1H) |
60% | at 130℃; for 1 h; | A mixture of 1 (1.0 g, 4.9 mmol) and POCl3 (0.68 mL, 7.3mmol) was heated at 130 °C (bath) for 1 h. The resulting liquid was allowed to cool and was stirred with CH2Cl2 (10 mL) and aqueous NH3 (25percent; 10 mL). The organic layer was washed with H2O (10 mL), dried over MgSO4 and the solvent removed. The residue was dissolved in a mixture of t-BuOMe (5 mL) and CH2Cl2 (2 mL) at 50 °C (bath), and the solution was kept at –30 °C overnight. The resulting crystals were collected and dried (0.65 g, 60percent); mp. 132–133 °C (lit.15,19 130–131 °C); IR (neat): 1470, 1221, 1139,1006, 853 cm–1; 1H NMR (300 MHz, CDCl3) δ 4.02 (s, 3H), 4.03 (s, 3H), 7.33 (d, J = 4.9 Hz, 1H), 7.36 (s,1H), 7.42 (s, 1H), 8.54 (d, J = 4.9 Hz, 1H); 13C NMR (75 MHz, CDCl3) δ 56.4, 56.5, 101.9, 108.1, 119.8,122.3, 140.9, 146.1, 147.4, 151.0, 153.4; HRMS (FAB) m/z 224.0434 (calcd 224.0473 for C11H11NO2Cl,[M+H]+). |
35% | Stage #1: for 1 h; Heating / reflux Stage #2: With ammonium hydroxide In water |
Step 2: 4-Chloro-6,7-dimethoxyquinoline (4) A suspension of the quinolone 3 (6.54 g, 31.9 mmol) in SOCl2 (70 ml) and DMF (cat) was heated to reflux for 1 hr. The reaction mixture was cooled to room temperature and concentrated. The residue was basified with NH4OH solution and then extracted with DCM. The extract was dried over anhydrous Na2SO4, filtered then concentrated. The residue was purified by column chromatography (eluent a gradient of 20percent EtOAc/hexane to 100percent EtOAc) to afford title compound 4 (2.5 g, 35percent yield) as a brown solid. LRMS (M+1): 224.1 (75percent)/226.1 (25percent). |
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