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CAS No. : | 73987-38-9 | MDL No. : | MFCD00047612 |
Formula : | C12H11NO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | SVHHAAQTOHCWJX-UHFFFAOYSA-N |
M.W : | 201.22 | Pubchem ID : | 94670 |
Synonyms : |
|
Num. heavy atoms : | 15 |
Num. arom. heavy atoms : | 10 |
Fraction Csp3 : | 0.17 |
Num. rotatable bonds : | 3 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 57.83 |
TPSA : | 39.19 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) : | -5.65 cm/s |
Log Po/w (iLOGP) : | 2.37 |
Log Po/w (XLOGP3) : | 2.64 |
Log Po/w (WLOGP) : | 2.41 |
Log Po/w (MLOGP) : | 1.91 |
Log Po/w (SILICOS-IT) : | 2.65 |
Consensus Log Po/w : | 2.4 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.05 |
Solubility : | 0.181 mg/ml ; 0.000899 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.11 |
Solubility : | 0.155 mg/ml ; 0.00077 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -4.19 |
Solubility : | 0.0131 mg/ml ; 0.000065 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.44 |
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 |
---|---|---|
89% | for 8 h; Heating / reflux | [0345] A solution of 6-quinolinecarboxylic acid (9.50 g, 54.9 mmol) and 2 ml of concentrated sulfuric acid in ethanol (250 ml) was refluxed for 8 h. The solvent was evaporated and the residue was taken up in water. After adjustment of the pH to 8 by the addition of potassium hydroxide the product was collected by filtration and dried in vacuum. Yield 9.85 g (89percent) of ethyl 6-quinolinecarboxylate as a pale brown solid. M.p.: 66-67° C., TLC (CH2Cl2/MeOH/AcOH 9:0.5:0.1): Rf 0.52 [0346] A solution of ethyl 6-quinolinecarboxylate (9.80 g, 48.7 mmol) was acidified to pH 2 by the addition of 1N aqueous HCl. After addition of 20percent Pd-Mohr catalyst (1.96 g) the solution was hydrogenated at 60° C. under 3 bar of hydrogen pressure for 17 h. The reaction mixture was filtered through celite. The filtrate was evaporated and the residue was taken up in ethyl acetate and water. The pH was adjusted to 16 by the additon of 1 N aqueous potassium hydroxide. The phases were separated and the organic phase was washed with brine, dried over Na2SO4 and evaporated. Yield 8.72 g (87percent) of ethyl 1,2,3,4-tetrahydro-6-quinolinecarboxylate as a pale brown solid. M.p.: 68-70° C., GC-MS: [M+]=205. |
81% | Reflux | To a solution of quinoline-6-carboxylic acid (2.8 g, 16 mmol) in ethanol (100 mL) was added concentrated sulfuric acid (2 mL). The reaction was heated to reflux overnight. The solvent was evaporated to give a brown residue that was taken up in ethyl acetate (150 mL). The mixture was washed with water (2.x.30 mL), saturated aqueous sodium bicarbonate (2.x.30 mL), and brine (2.x.30 mL). The organic layer was dried over sodium sulphate, filtered, and concentrated to an oil. Purification by flash column chromatography gave the title compound (2.0 g, 81percent) as a brown solid. |
75% | Stage #1: at 80℃; for 48 h; Stage #2: With sodium hydroxide; ammonia In water |
Example 66: Synthesis of 6-f3-(2.4-dimethoχybenzylidene)-3A5,6- tetrahydropyridin-2-yl)quinoline hydrochloride.; The preparation of 6-(3-(2,4-dimethoxybenzylidene)-3,4,5,6- tetrahydropyridin-2-yl)quinoline hydrochloride is described below.; A. Step 1: Preparation of Intermediate 14; Intermediate 14 was prepared as described in EP 0381375 Bl, page 21. 6- quinolinecarboxylic acid (12.2 g, 70.4 mmol) was suspended into ethanol (70 mL) in a reaction vessel. Concentrated sulfuric acid (12 mL) was added, the reaction vessel was sealed and the reaction was heated to 800C for 48 hours. The reaction was then cooled to room temperature, partially concentrated under reduced pressure and treated with concentrated ammonium hydroxide and 1 NNaOH(aq) until pH = 9. This produced an oil that separated from solution. This mixture was extracted three times with EtOAc. The EtOAc extracts were then washed with brine, combined, iσ dried over Na2SO4, filtered, concentrated under reduced pressure giving a green oil. This oil was filtered through a 9.5 cm x 3.0 cm plug of silica gel with 50percent EtOAc : hexane. The filtrate was concentrated under reduced pressure and dried under vacuum giving 10.66g (75percent) of a light green oil. 1H NMR (DMSO-rf6) δ 9.03 (dd, IH, J = 4.27, 1.70 Hz), 8.70 (d, IH, J= 1.71 Hz), 8.60 (broad d, IH5 J= 8.12 Hz),15 8.22 (dd, IH, J= 8.54, 1.71 Hz), 8.11 (d, IH, J= 8.97 Hz)3 7.64 (dd, 1H, J= 8.12, 4.27 Hz), 4.40 (q, 2H, J= 7.26 Hz), 1.38 (t, 3H, J= 7.26 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | With Au/Al2O3 In 1,2-dichloro-ethane at 70℃; for 48 h; | General procedure: Au/Al2O3 (20 mg of 1percent, 0.2 mg Au, 0.001 mmol, 2 mol percent) was added in the solution of N-propargylaniline (4a) (6.5 mg, 0.05 mmol) in DCE (1 mL) and the mixture was heated at 70 °C for 24 h. More Au/Al2O3 (20 mg of 1percent, 0.2 mg Au, 0.001 mmol, 2 mol percent, total 4 mol percent) was then added and the mixture was heated for 24 h more. After the filtration of the catalyst through silica gel layer, evaporation of the solvent and separation by column chromatography [silica gel, hexane/ethyl acetate (4:1) the quinoline (5a) was received as light yellow oil (5.8 mg, 90percent yield) followed by the biquinoline 6a (0.45 mg, 8percent yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45% | at 150℃; for 12 h; Green chemistry | Accurately weigh 0.005mmol (l. Lmg) of the transition metal, add 10mL has been put into the magnetic stirrer Young's reaction tube, The oxygen reaction was carried out in the Young's reaction tube, and the reaction was carried out under oxygen conditions. The syringe was applied to the Young's reaction tubeA solution of 0.04 mmol of co-catalyst I, 0.08 mmol of co-catalyst II, 0.2 mmol of 4-carboxylate and 1 ml of l-3'-propylene glycol, the above-mentioned Young's reaction tube was placed on a magnetic stirrer and stirred at 150 ° C for 12 h. After the reaction was completed,The pH of the solution was neutral, and the reaction solution was post-treated to obtain pure product of ethyl 6-formate quinoline in a yield of 45percent. |
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