Purity | Size | Price | VIP Price | USA Stock *0-1 Day | Global Stock *5-7 Days | Quantity | |||||
{[ item.p_purity ]} | {[ item.pr_size ]} |
{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} |
{[ getRatePrice(item.pr_usd, 1,1) ]} | {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]} | {[ item.pr_usastock ]} | Inquiry - | {[ item.pr_chinastock ]} | Inquiry - |
* Storage: {[proInfo.prStorage]}
CAS No. : | 59394-27-3 | MDL No. : | MFCD06407627 |
Formula : | C10H6ClNO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | LZJIPAFEFGRTQS-UHFFFAOYSA-N |
M.W : | 191.61 | Pubchem ID : | 1548875 |
Synonyms : |
|
Num. heavy atoms : | 13 |
Num. arom. heavy atoms : | 10 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 52.14 |
TPSA : | 29.96 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) : | -5.5 cm/s |
Log Po/w (iLOGP) : | 1.52 |
Log Po/w (XLOGP3) : | 2.77 |
Log Po/w (WLOGP) : | 2.7 |
Log Po/w (MLOGP) : | 1.7 |
Log Po/w (SILICOS-IT) : | 3.22 |
Consensus Log Po/w : | 2.38 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.28 |
Solubility : | 0.101 mg/ml ; 0.000529 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.05 |
Solubility : | 0.169 mg/ml ; 0.000881 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -4.27 |
Solubility : | 0.0103 mg/ml ; 0.000054 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.25 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P305+P351+P338-P304+P340 | 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 |
---|---|---|
92% | With selenium(IV) oxide In 1,4-dioxane at 60℃; Inert atmosphere; | |
84% | With selenium(IV) oxide In 1,4-dioxane for 2.5h; Heating; | |
78% | With selenium(IV) oxide; water In tetrahydrofuran at 25℃; for 6h; |
76% | With [bis(acetoxy)iodo]benzene In dimethyl sulfoxide at 120℃; for 0.5h; Microwave irradiation; Sealed tube; Green chemistry; regioselective reaction; | Experimental Procedures Typical experimental procedure for oxidation of 2-methylquinolines General procedure: Unless otherwise noted, reactions were carried out as following: 2-methylquinolines 1 (2 mmol), PIDA (4 mmol), DMSO(10 mL) were mixed in a sealed microwave tube. The reaction mixture was stirred at 120 °C for 30 min under microwave irradiation using a CEM Discover microwave reactor (the highest power: 85 W; run time: 10 min; hold time: 30 min; temperature: 120 °C). The resulting reaction mixture was neutralized with saturated aqueous NaHCO3 solution and extracted with Et2O. The combined organic layers were washed with H2O and dried over Na2SO4, then concentrated under reduced pressure. The crude residue was purified by flash chromatographyon silica gel using hexane/EtOAc as eluent. |
62% | With copper(II) choride dihydrate; oxygen In N,N-dimethyl-formamide at 130℃; for 5h; Sealed tube; | |
With V2O5#dotMoO3; silica gel at 380 - 400℃; mit Wasserdampf und Luft; | ||
With iodine; dimethyl sulfoxide at 110℃; for 1h; | General Procedure General procedure: In a 25 mL round bottom flask equipped with a magnetic stir bar, The 2-methylquinoline (80 mg, 0.56 mmol) was dissolved in DMSO (4 mL) and molecular iodine (20 mol%)) was added and heated at 110 °C for 1 h. Next, o-phenylenediamine (0.56 mmol) was added and the resulting solution stirred continuous for 7 h. After this time, the reaction mixture was cooled to room temperature, quenched with saturated solution of Na2S2O3 (20 mL) and the reaction was extracted with ethyl acetate (3x 20 mL). The combined organic phase was dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was purified by chromatography on silica gel using Petroleum ether as eluent to provide 3a-u and 5a-g. | |
With iodine; dimethyl sulfoxide at 110℃; Sealed tube; | Standard procedure for the synthesis of 5-(quinolin-2-yl)-1,3,4-oxadiazoles General procedure: A 25 mL pressure vial was charged with 2-methylquinoline (1a) (71.5 mg, 0.50 mmol, 1.0 equiv.), I2 (317.3 mg, 1.25 mmol, 2.5 equiv.) and DMSO (3.0 mL). The vial was sealed and the resulting mixture was stirred at 110 °C for 4-6 h under an air atmosphere, after disappearance of the reactant (monitored by TLC), then added benzohydrazide (2a) (81.6 mg, 0.6 mmol, 1.2 equiv.) , K2CO3 (414.0 mg, 3.0 mmol, 6.0 equiv.) at 110 °C for another 4-6 h. After the reaction completed, and added 50 mL water to the mixture, then extracted with EtOAc 3 times (3 × 50 mL). The extract was washed with 10% Na2S2O3 solution (w/w), dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was puried by flash column chromatography on silica gel to yield the corresponding product 3aa as a yellow solid (72% yield). | |
With selenium(IV) oxide In 1,4-dioxane at 100℃; | ||
With iodine; dimethyl sulfoxide at 110℃; Sealed tube; | ||
With iodine; dimethyl sulfoxide; trifluoroacetic acid at 130℃; for 3h; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48% | With pyridinium p-toluenesulfonate In toluene for 8h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With pyridinium p-toluenesulfonate In toluene for 10h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
entspr. 2-CH3-Chinolin Ig, SeO2; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 60 percent / pyridinium tosylate / toluene / 10 h / Heating 2: 68 percent / NaOH / H2O; methanol / 4 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 48 percent / pyridinium tosylate / toluene / 8 h / Heating 2: 80 percent / NaOH / H2O; methanol / 3.5 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | In methanol; water at 0 - 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: methanol / 20 °C / Inert atmosphere 2.1: sodium tetrahydroborate / 3.17 h / 0 - 20 °C / Inert atmosphere 2.2: 0 °C / Inert atmosphere 3.1: triethylamine / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere 4.1: 1,1'-binaphthyl-2,2'-diyl hydrogenphosphate; diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate / dichloromethane / 16 h / 20 °C / Inert atmosphere; Schlenk technique |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: methanol / 20 °C / Inert atmosphere 2.1: sodium tetrahydroborate / 3.17 h / 0 - 20 °C / Inert atmosphere 2.2: 0 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: methanol / 20 °C / Inert atmosphere 2.1: sodium tetrahydroborate / 3.17 h / 0 - 20 °C / Inert atmosphere 2.2: 0 °C / Inert atmosphere 3.1: triethylamine / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / 0 - 5 °C 1.2: 4 h / 0 - 15 °C 2.1: palladium diacetate; triphenylphosphine; triethylamine / N,N-dimethyl-formamide / 110 °C 3.1: caustic lye / 12 h / 120 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / 0 - 5 °C 1.2: 4 h / 0 - 15 °C 2.1: palladium diacetate; triphenylphosphine; triethylamine / N,N-dimethyl-formamide / 110 °C 3.1: caustic lye / 12 h / 120 °C 4.1: sodium hydroxide / methanol / 1 h / 25 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | Stage #1: Methyltriphenylphosphonium bromide With n-butyllithium In tetrahydrofuran; hexane at 0 - 5℃; for 1h; Stage #2: 7-chloro-quinoline-2-carbaldehyde In tetrahydrofuran; hexane; dichloromethane at 0 - 15℃; for 4h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With piperidine In ethanol at 50℃; for 12h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: hydrogenchloride / water; toluene / 1.5 h / 110 °C 1.2: 1 h / 60 °C / Cooling with ice 2.1: selenium(IV) oxide / 1,4-dioxane / 60 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: piperidine / ethanol / 12 h / 50 °C / Inert atmosphere 2: potassium hydroxide / water; ethanol / 2 h / 80 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: piperidine / ethanol / 12 h / 50 °C / Inert atmosphere 2: potassium hydroxide / water; ethanol / 2 h / 80 °C / Inert atmosphere 3: 20 °C / pH 3 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
at 110℃; for 7h; | General Procedure General procedure: In a 25 mL round bottom flask equipped with a magnetic stir bar, The 2-methylquinoline (80 mg, 0.56 mmol) was dissolved in DMSO (4 mL) and molecular iodine (20 mol%)) was added and heated at 110 °C for 1 h. Next, o-phenylenediamine (0.56 mmol) was added and the resulting solution stirred continuous for 7 h. After this time, the reaction mixture was cooled to room temperature, quenched with saturated solution of Na2S2O3 (20 mL) and the reaction was extracted with ethyl acetate (3x 20 mL). The combined organic phase was dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was purified by chromatography on silica gel using Petroleum ether as eluent to provide 3a-u and 5a-g. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
at 110℃; for 7h; | General Procedure General procedure: In a 25 mL round bottom flask equipped with a magnetic stir bar, The 2-methylquinoline (80 mg, 0.56 mmol) was dissolved in DMSO (4 mL) and molecular iodine (20 mol%)) was added and heated at 110 °C for 1 h. Next, o-phenylenediamine (0.56 mmol) was added and the resulting solution stirred continuous for 7 h. After this time, the reaction mixture was cooled to room temperature, quenched with saturated solution of Na2S2O3 (20 mL) and the reaction was extracted with ethyl acetate (3x 20 mL). The combined organic phase was dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was purified by chromatography on silica gel using Petroleum ether as eluent to provide 3a-u and 5a-g. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
at 110℃; for 7h; | General Procedure General procedure: In a 25 mL round bottom flask equipped with a magnetic stir bar, The 2-methylquinoline (80 mg, 0.56 mmol) was dissolved in DMSO (4 mL) and molecular iodine (20 mol%)) was added and heated at 110 °C for 1 h. Next, o-phenylenediamine (0.56 mmol) was added and the resulting solution stirred continuous for 7 h. After this time, the reaction mixture was cooled to room temperature, quenched with saturated solution of Na2S2O3 (20 mL) and the reaction was extracted with ethyl acetate (3x 20 mL). The combined organic phase was dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was purified by chromatography on silica gel using Petroleum ether as eluent to provide 3a-u and 5a-g. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
at 110℃; for 7h; | General Procedure General procedure: In a 25 mL round bottom flask equipped with a magnetic stir bar, The 2-methylquinoline (80 mg, 0.56 mmol) was dissolved in DMSO (4 mL) and molecular iodine (20 mol%)) was added and heated at 110 °C for 1 h. Next, o-phenylenediamine (0.56 mmol) was added and the resulting solution stirred continuous for 7 h. After this time, the reaction mixture was cooled to room temperature, quenched with saturated solution of Na2S2O3 (20 mL) and the reaction was extracted with ethyl acetate (3x 20 mL). The combined organic phase was dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was purified by chromatography on silica gel using Petroleum ether as eluent to provide 3a-u and 5a-g. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
at 110℃; for 7h; | General Procedure General procedure: In a 25 mL round bottom flask equipped with a magnetic stir bar, The 2-methylquinoline (80 mg, 0.56 mmol) was dissolved in DMSO (4 mL) and molecular iodine (20 mol%)) was added and heated at 110 °C for 1 h. Next, o-phenylenediamine (0.56 mmol) was added and the resulting solution stirred continuous for 7 h. After this time, the reaction mixture was cooled to room temperature, quenched with saturated solution of Na2S2O3 (20 mL) and the reaction was extracted with ethyl acetate (3x 20 mL). The combined organic phase was dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was purified by chromatography on silica gel using Petroleum ether as eluent to provide 3a-u and 5a-g. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
at 110℃; for 7h; | General Procedure General procedure: In a 25 mL round bottom flask equipped with a magnetic stir bar, The 2-methylquinoline (80 mg, 0.56 mmol) was dissolved in DMSO (4 mL) and molecular iodine (20 mol%)) was added and heated at 110 °C for 1 h. Next, o-phenylenediamine (0.56 mmol) was added and the resulting solution stirred continuous for 7 h. After this time, the reaction mixture was cooled to room temperature, quenched with saturated solution of Na2S2O3 (20 mL) and the reaction was extracted with ethyl acetate (3x 20 mL). The combined organic phase was dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was purified by chromatography on silica gel using Petroleum ether as eluent to provide 3a-u and 5a-g. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate In dimethyl sulfoxide at 110℃; Sealed tube; | Standard procedure for the synthesis of 5-(quinolin-2-yl)-1,3,4-oxadiazoles General procedure: A 25 mL pressure vial was charged with 2-methylquinoline (1a) (71.5 mg, 0.50 mmol, 1.0 equiv.), I2 (317.3 mg, 1.25 mmol, 2.5 equiv.) and DMSO (3.0 mL). The vial was sealed and the resulting mixture was stirred at 110 °C for 4-6 h under an air atmosphere, after disappearance of the reactant (monitored by TLC), then added benzohydrazide (2a) (81.6 mg, 0.6 mmol, 1.2 equiv.) , K2CO3 (414.0 mg, 3.0 mmol, 6.0 equiv.) at 110 °C for another 4-6 h. After the reaction completed, and added 50 mL water to the mixture, then extracted with EtOAc 3 times (3 × 50 mL). The extract was washed with 10% Na2S2O3 solution (w/w), dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was puried by flash column chromatography on silica gel to yield the corresponding product 3aa as a yellow solid (72% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | Stage #1: meta-bromobenzyl bromide With triphenylphosphine In N,N-dimethyl-formamide at 0 - 120℃; for 2.5h; Stage #2: With sodium methylate In N,N-dimethyl-formamide at 0℃; for 0.5h; Stage #3: 7-chloro-quinoline-2-carbaldehyde In N,N-dimethyl-formamide at 0 - 20℃; for 1h; | 1-3 Example 1: Synthesis of compound of formula (II) Dissolve 3-bromobenzyl bromide (97.8g, 391.4mmol) and triphenylphosphonium (102.7g, 391.4mmol) in DMF (500mL), heat to 120°C, stir for 2h, cool to 0°C and stir for 30min , Sodium methoxide (42.3g, 782mmol) was added and stirred for 30min, then the compound of formula (IV) (50g, 260.9mmol) was slowly added, the temperature was gradually raised to room temperature, the reaction was carried out for 1h, and TLC detected that the raw material reaction was complete. The reaction solution was poured into 1L of 1mol/L dilute hydrochloric acid, and 1L of ethyl acetate was added for extraction. The organic phase was washed with saturated sodium bicarbonate solution and brine in turn, and the organic phase was collected, dried, decolorized, and concentrated under reduced pressure. The concentrated solution was added to ice water, stirred for 30min, the solid gradually precipitated, filtered, and rinsed with sodium bicarbonate aqueous solution and methyl tert-butyl ether in turn to obtain 73.8g of the compound of formula (II), the yield was 82%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | With rhodium (II) octanoate dimer In dichloromethane at 110℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
141 mg | With potassium carbonate at 110℃; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | Stage #1: 7-chloro-quinoline-2-carbaldehyde; ammonium thiocyanate; benzylamine In dimethyl sulfoxide at 20℃; for 0.0833333h; Stage #2: With iodine pentoxide In dimethyl sulfoxide at 100℃; for 5h; | 32 Example 32: Synthesis of 3-cyano-8-chloro-1-phenylimidazo[1,5-a]quinoline In a dry reactor, NH4SCN (0.6 mmol, 46 mg), 7-chloroquinoline-2-carbaldehyde (0.3 mmol) and benzylamine (0.6 mmol) were added and then dimethyl sulfoxide (2 mL) was added.After stirring the mixture at room temperature for 5 min, I 2 O 5 (0.3 mmol, 100 mg) was added, and the mixture was further stirred at 100° C. for 5 h.After the reaction (TLC) was completed, the reaction mixture was allowed to cool to room temperature and quenched with saturated Na2S2O3 solution.Then the reaction mixture was extracted with ethyl acetate.The organic phase was dried over anhydrous Na2SO4, and concentrated under reduced pressure to obtain a crude residue.Finally, the organic phase is concentrated on a rotary evaporator.Crude product is purified by column chromatography3-cyano-8-chloro-1-phenylimidazo[1,5-a]quinoline is obtained.Yield: 55%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
113 mg | Stage #1: 7-chloro-quinoline-2-carbaldehyde With iodine; dimethyl sulfoxide; trifluoroacetic acid at 130℃; for 3h; Inert atmosphere; Stage #2: edaravone Inert atmosphere; |
[ 59394-26-2 ]
6-Chloroquinoline-2-carbaldehyde
Similarity: 0.98
[ 53590-59-3 ]
6-Chloro-1H-indole-2-carbaldehyde
Similarity: 0.95
[ 27932-08-7 ]
4-Chloro-1H-indole-2-carbaldehyde
Similarity: 0.93
[ 59394-26-2 ]
6-Chloroquinoline-2-carbaldehyde
Similarity: 0.98
[ 53590-59-3 ]
6-Chloro-1H-indole-2-carbaldehyde
Similarity: 0.95
[ 59394-26-2 ]
6-Chloroquinoline-2-carbaldehyde
Similarity: 0.98
[ 53590-59-3 ]
6-Chloro-1H-indole-2-carbaldehyde
Similarity: 0.95
[ 27932-08-7 ]
4-Chloro-1H-indole-2-carbaldehyde
Similarity: 0.93
[ 59394-26-2 ]
6-Chloroquinoline-2-carbaldehyde
Similarity: 0.98
[ 53590-59-3 ]
6-Chloro-1H-indole-2-carbaldehyde
Similarity: 0.95
[ 59394-26-2 ]
6-Chloroquinoline-2-carbaldehyde
Similarity: 0.98
[ 59394-28-4 ]
8-Chloroquinoline-2-carbaldehyde
Similarity: 0.89
[ 59394-26-2 ]
6-Chloroquinoline-2-carbaldehyde
Similarity: 0.98
[ 59394-28-4 ]
8-Chloroquinoline-2-carbaldehyde
Similarity: 0.89