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CAS No. : | 72-80-0 | MDL No. : | MFCD00023984 |
Formula : | C10H7Cl2NO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | GPTXWRGISTZRIO-UHFFFAOYSA-N |
M.W : | 228.07 | Pubchem ID : | 6301 |
Synonyms : |
Chloquinan
|
Num. heavy atoms : | 14 |
Num. arom. heavy atoms : | 10 |
Fraction Csp3 : | 0.1 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 58.75 |
TPSA : | 33.12 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) : | -5.21 cm/s |
Log Po/w (iLOGP) : | 2.37 |
Log Po/w (XLOGP3) : | 3.49 |
Log Po/w (WLOGP) : | 3.56 |
Log Po/w (MLOGP) : | 2.6 |
Log Po/w (SILICOS-IT) : | 3.66 |
Consensus Log Po/w : | 3.13 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.98 |
Solubility : | 0.0238 mg/ml ; 0.000104 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.87 |
Solubility : | 0.0309 mg/ml ; 0.000135 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -4.75 |
Solubility : | 0.00404 mg/ml ; 0.0000177 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.6 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302 | 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 |
---|---|---|
97.7% | With hydrogenchloride; sodium hypochlorite In water at 20 - 30℃; for 4.5 h; | In a 1000 ml three-neck bottle, 500 g of 15 wt.percent hydrochloric acid and 20 g of 8-hydroxy-2-methylquinoline were added, and the temperature was lowered to 25 ° C, and 190 g of a 10 wt.percent aqueous solution of sodium hypochlorite was added dropwise, and the dropping time was controlled for 4 hours. During the dropping process, the reaction temperature is controlled to 20 to 30 ° C. After the addition is completed, Insulation for 0.5 hours, suction filtration to obtain wet product; The wet product is put into 200 ml of purified water, and the pH is adjusted to 4 to 5 with sodium carbonate, and suction filtration is performed. Rinse and dry to obtain a crude product, refined with 200 ml of methanol and 600 ml of purified water. 28.0 g of chloroquinadol was obtained, the yield was 97.7percent, and the HPLC purity was 99.63percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With selenium(IV) oxide; In 1,4-dioxane; at 50 - 80℃; for 3h; | A solution of 5, 7-dichloro-2-methyl-quinolin-8-ol 16 (1.5 g, 6.58 mmol) in 1,4- dioxane (20 mL) was added dropwise over 3 h to a stirred suspension of selenium dioxide (1. 3 g, 11.72 mmol) in 1,4-dioxane (60 mL) at [50-55 C. THE] resulting mixture was then heated at [80] [C] overnight, cooled, and the solids filtered off (celite). The filtrate was concentrated and the residue, after washing with diethyl ether (10 mL x 3), gave 17 as a yellow solid (quantitative yield). This material was used in the subsequent step without further purification. [1H NMR] [(CDC13,] 400 MHz): [6] 10.26 (s, 1 H), 8.69 (d, [J=8.] 8,1 H), 8.37 (br, 1 H), 8. 17 [(D,] J=8. 8, [1] H), 7.76 (s, [1] H). |
2.1 g | With selenium(IV) oxide; In 1,4-dioxane; at 55 - 80℃; | [0214] To a stirred suspension of selenium dioxide (1.75 g, 15.80 mmol) in 1,4-dioxane (80 mL) at 55C was added a solution of 5,7-dichloro-2-methyl-quinolin-8-ol (2.0 g, 8.77 mmol) in 1,4-dioxane (20 mL) in a dropwise manner over a period of 3 h. After complete addition, the heating temperature was raised to 80C, and heating was maintained overnight. The reaction mixture was then allowed to cool down to room temperature and the insoluble solids were filtered off on a celite bed. The filtrate was concentrated under vacuum, and the residue was washed with diethyl ether (10 mL x 3) to yield 2.10 g (quantitative yield) of the aldehyde 2 as a yellow powder, which was used in the following step without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium iodide; potassium carbonate; In water; butanone; | EXAMPLE 1 2-Methyl-5,7-dichloro-8-(cyanomethoxy)-quinoline (Compound No. 18) 10.7 g of 5,7-dichloro-8-hydroxyquinaldine are dissolved at elevated temperature in 150 ml of 2-butanone; 10.4 g of potassium carbonate are then added portionwise, and the mixture is refluxed for one hour. After the addition of 1 g of potassium iodide, there are added dropwise, with stirring and refluxing, 7.1 g of chloroacetonitrile in 30 ml of 2-butanone, and the mixture is subsequently heated for 3 hours at an internal temperature of 75 C. To the resulting reaction mixture, after cooling to room temperature, is added 1 liter of water, and the whole is filtered; the residue is washed with water, dried, and recrystallized from chloroform/petroleum ether (40-60 C.) to thus obtain 2-methyl-5,7-dichloro-8-(cyanomethoxy)-quinoline, m.p. 157-158 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In a glove box, tetrachlorozirconium (0.23 g) was dissolved in 10 mL methanol (gets hot) and added to 0.92 g 5,7-dichloro-2-methyl-8-hydroxyquinoline (Aldrich) also dissolved in 10 mL methanol with stirring. The solution immediately turned yellow and became warm. 0.45 g sodium t-butoxide solid was slowly added and the solution became hot with a yellow ppt. This mixture was refluxed for 15 mins in the glove box at which point the solution was bright yellow with a yellow ppt. The yellow solid was collected by filtration and then redissolved into methylene chloride, filtered and evaporated to dryness in vacuo. The collected yellow solid was blue-green photoluminescent and soluble in toluene. Material is purified for device work via high vacuum sublimation |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
To a solution of 5, 7-Dichloro-2-methyl-quinolin-8-ol (2.95 g, 12.93 mmol) in 1,4-dioxane (65 mL) was added dry NaH (1.02 g, 42.5 mmol) with the evolution of H2 gas. Cesium carbonate (13.9 g, 42. 7 mmol) was added and the yellow suspension was stirred at rt for 30 min then 2-bromo-2- methylpropanamide (7.1 g, 42.7 mmol) was added and the reaction was heated to 110 C under argon for 20 h. After removing from the heat, NMP (70 mL) , 1, 3 -dimethyl 3,4,5,6- tetrahydro-lH-pyrimidone (7.6 mL) were added followed by the addition of dry NaH (380 mg, 15 .8 mmol) and the reaction was heated to 150 C for 3 days. Cooled and partitioned between EtOAc and H2O the mixture was extracted into EtOAc (x3) . The combined organic layers were washed with H2O, brine, dried Na2SO4, filtered, concentrated and purified by flash chromatography eluting with 10%- 20%EtOAc/petroleum ether 40-60C to provide the 5,7- Dichloro-2-methyl-quinolin-8-yl amine 3 as a tan solid (941 mg, 32%). x H NMR (400 MHz, d6-DMSO) delta.2.68 (s, 3H, CH3), 6.07 (s, 2H, NH2), 7.57 (s, IH, ArH), 7.59 (d,J-=8.8Hz, IH, ArH), 8.33 (d, J= 8.8 Hz, IH, ArH). MS: m/z 227.2 [M+H] + .Further elution of the column with 30% then 40% EtOAc/ petroleum ether 40-60C afforded the amide 2 (1.95 g, 48%) as a crystalline white solid. 1H NMR (400 MHz, d6-DMSO) delta.1.43 (s, 6H, 2xCH3) , 2.69 (s, 3H, CH3), 5.83 (s, IH, OH), 7.64 (d, J=8.8Hz, IH, ArH), 7.91 (s, IH, ArH), 8.45 (d, |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
47% | at 180℃; for 0.166667h;Microwave irradiation; | General procedure: The appropriate quinaldine derivative(1 mmol) was mixed thoroughly with four equiv aldehyde, put in an open vessel and exposed to microwave irradiation for 10 min at 180 C. Then the reaction mixture was cool down to 0 C, the precipitate was filtered off. The solid was crystallized from ethanol. |
47% | at 180℃; for 0.166667h;Microwave irradiation; | 5,7-Dichloro-8-hydroxyquinaldine (1.0 mmol) was mixed thoroughly with 4 equiv. of 2-chorobenzaldehyde, put in an open vessel and exposed to microwave irradiation for 10 min. at 180 C and 50 W. The reaction mixture was cool down to 0 C, and the precipitate was filtered off. The solid was crystallized from ethanol. It gave beige crystals. Yield: 47%, m.p. 205-210 C. m/z = 348.27 [M]-; HPLC purity 98.74%; UV (nm), lambdamax/log epsilon: 319.9/3.61. 1H NMR (400 MHz, DMSO-d6): delta = 8.48 (d, J = 8.7 Hz, 1 H); 8.36 (d, J = 16.2 Hz, 1 H); 7.98 (d, J = 8.8 Hz, 1 H); 7.94 (dd, J = 7.6, 2.0 Hz, 1 H); 7.77 (s, 1 H); 7.58-7.50 (m, 2 H); 7.47-7.36 (m, 2 H) ppm. 13C NMR (100 MHz, DMSO-d6): delta = 155.17, 149.33, 139.39, 134.81, 133.99, 133.57, 132.06, 131.14, 130.83, 130.44, 128.27, 128.17, 127.85, 124 37, 123.01, 119.63, 116.28 ppm. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate; In acetone; for 24h;Reflux; | General procedure: General procedure: To a solution of 8-hydroxyquinoline 4 (7 mmol) and (2-methyl)allyl bromide (10.5 mmol, 1.5 equiv) in acetone (30 mL) was added potassium carbonate (21 mmol, 3 equiv). After stirring for 24 h at reflux temperature, the reaction mixture was poured into water (15 mL) and extracted with dichloromethane (3 × 15 mL). The combined organic extracts were dried over anhydrous magnesium sulfate. Filtration of the drying agent and removal of the solvent in vacuo afforded the crude products 5a-n, which were purified by recrystallization. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With dmap; triethylamine; In tetrahydrofuran; at 80℃; for 12h;Inert atmosphere; | A mixture of 5,7-dichloro-2-methylquinolin-8-ol (10.0 g, 43.8 mmol), Boc20 (19.1 g, 2.0 equiv.), Et3N (9.14 mL, 1.5 equiv.) and DMAP (107 mg, 0.02 equiv.) in THF (50 mL) was heated with stirring to 80 C for 12 h under Argon. The mixture was then cooled to room temperature, and concentrated in vacuo. The crude was washed with water to yield the desired product (13.0 g, 39.6 mmol) as a white solid in 90% yield and used in the subsequent step without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
at 130℃; for 16h;Inert atmosphere; | The appropriate quinoline derivative (2.5 mmol) in acetic anhydride was thoroughly mixed with two equiv aldehyde and heated in an inert gas atmosphere (N2) for 16 h at 130C. Then, the mixture was evaporated to dryness and a solid was crystallized from EtOH. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
at 130℃; for 16h;Inert atmosphere; | The appropriate quinoline derivative (2.5 mmol) in acetic anhydride was thoroughly mixed with two equiv aldehyde and heated in an inert gas atmosphere (N2) for 16 h at 130C. Then, the mixture was evaporated to dryness and a solid was crystallized from EtOH. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
44% | With acetic acid; at 130℃;Inert atmosphere; | General procedure: The appropriate quinoline derivative(2.5 mmol) in acetic anhydride with 80% acetic acid was thoroughlymixed with one equivalent aldehyde and heated in an inert gasatmosphere (N2) for 18e22 h at 130 C. Then, the mixture wasevaporated to dryness and a solid was crystallized from ethanol, methanol or ethyl acetate |
at 130℃; for 16h;Inert atmosphere; | The appropriate quinoline derivative (2.5 mmol) in acetic anhydride was thoroughly mixed with two equiv aldehyde and heated in an inert gas atmosphere (N2) for 16 h at 130C. Then, the mixture was evaporated to dryness and a solid was crystallized from EtOH. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With water-d2; benzoic acid; at 120℃; for 4h; | 0.20 mmol of 8-hydroxy-5,7-dichloro-2-methylquinoline, 0.2 mL of D2O, 0.02 mmol was added to the reactorbenzoic acid. In a nitrogen/air atmosphere, heat to 120C, continue stirring for 4h, stop the reaction, cool to room temperature, add saturationThe sodium bicarbonate solution is washed, extracted with ethyl acetate, dried over sodium sulfate, and the solvent is distilled off under reduced pressure to obtain the target product.Yield 91%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
51% | In water; at 80℃; for 85h;Sealed tube; | 45 mg (about 0.2 mmol)Ligand 2-methyl-5,7-dichloro-8-hydroxyquinoline and 46 mg (about 0.1 mmol)Dy (NO3) 3 · 6H2O was addedOne end closed about 18 cm in the Pyrex tube,1.20 mL of a mixed solvent consisting of N, N-dimethylformamide and water was added(Volume ratio of N, N-dimethylformamide and water is 5: 1)A drop of 2 drops of triethylamine (where the pH of the solution was 7.1)Extract the Pyrex tube and seal the other end.The sealed Pyrex tube was incubated at 80 C for 85 h,Remove, naturally cooled to room temperature, can be observed at the bottom of the Pyrex tube with yellow strip crystal precipitation.Yield 48.9%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With triethylamine; In water; at 80℃; for 72h;pH 7.1;Sealed tube; | 45 mg (about 0.2 mmol)The ligand 2-methyl-5,7-dichloro-8-hydroxyquinoline and 46 mg (about 0.1 mmol)Dy (NO3) 3.6H2O was added to a Pyrex tube closed at one end with a length of about 18 cm. 2 mL of distilled water was added and 2 drops of triethylamine (at which time the solution had a pH of 7.1) was added. The Pyrex tube was evacuated and the other end seal.The Pyrex tube will be placed at 80 insulation reaction 72h, remove, cooled to room temperature, the bottom of the tube was observed Pyrex yellow crystal precipitation. Yield 63%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | Triethylamine (220 muL, 1.59 mmol) was added to 5,7-dichloro-8-hydroxyquinaldine [Compound 72] at room temperature(243 mg, 1.04 mmol) in acetonitrile (1 mL)After stirring for 10 minutes,1-(fluorosulfonyl)-2-3-dimethyl-1H-imidazole triflateA solution of [Compound 4] (420 mg, 1.28 mmol) in acetonitrile (1 mL) was added to the system in one portion and reacted under argon for 1 h.TLC (petroleum ether: ethyl acetate = 10:1, product Rf = 0.64) followed the reaction,Column chromatography purification (silica gel 300-400 mesh,Petroleum ether: ethyl acetate = 10:1),The pale green solid 5,7-dichloro-2-methyl-quinoline-8-oxylsulfonyl fluoride is obtained[Compound 73] (314 mg, 97%) (scheme 34). |
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P371 + P380 + P375 | In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion. |
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Disposal | |
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Physical hazards | |
Code | Phrase |
H200 | Unstable explosive |
H201 | Explosive; mass explosion hazard |
H202 | Explosive; severe projection hazard |
H203 | Explosive; fire, blast or projection hazard |
H204 | Fire or projection hazard |
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H220 | Extremely flammable gas |
H221 | Flammable gas |
H222 | Extremely flammable aerosol |
H223 | Flammable aerosol |
H224 | Extremely flammable liquid and vapour |
H225 | Highly flammable liquid and vapour |
H226 | Flammable liquid and vapour |
H227 | Combustible liquid |
H228 | Flammable solid |
H229 | Pressurized container: may burst if heated |
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H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
H240 | Heating may cause an explosion |
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H242 | Heating may cause a fire |
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H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
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H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
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H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
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H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
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H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
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H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
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H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
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