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CAS No. : | 30389-33-4 | MDL No. : | MFCD01862194 |
Formula : | C9H9NO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | UTTJAIFHRUAFED-UHFFFAOYSA-N |
M.W : | 163.17 | Pubchem ID : | 169153 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-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 |
---|---|---|
92.7% | With N-Bromosuccinimide In cyclohexane for 3 h; Cooling with ice; Reflux | To a 100 ml three-necked flask were added 3,4,7,8-tetrahydro-2,5 (1 H, 6Η) -quinoline dione (0.02 mol) and cyclohexane (25 ml) After stirring to dissolve in the ice bath for 10min, slowly add dropwise a solution of N-bromosuccinimide (0.03mol) in cyclohexane (5ml), and reflux for 3h at the end of the dropwise addition. After completion of the reaction by TLC, cool down to room temperature . Water was added (amount was 0.7 times the volume of the reactant), and the mixture was allowed to stand with stirring. The aqueous layer was extracted with ethyl acetate (1 × the volume of the aqueous layer 4 times), and the organic layers were combined. Anhydrous sulfuric acid Calcium was dried and filtered, the filtrate was evaporated to remove the solvent, and the residue was dried to give an off-white solid as a 5-hydroxy-Dihydro-2 (1H) -quinolone (Yield 92.7percent), mp 233 ~ 234 °C, BP2013-HPLC method chromatography purity 94.3percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62.3% | Stage #1: at 155 - 165℃; for 4 h; Stage #2: With methanol; sodium hydroxide In water at 20℃; for 1 h; Heating / reflux |
Example 2; Preparation of 7-HQ in the Presence of a Salt; A 0.5 l reactor was charged with 3-MPCA (40 g, 0.185 mole), AlCl3 (125 g, 0.925 mole, 5 eq.) and anhydrous sodium chloride (20 g) and the reaction mixture was heated under stirring to about 160° C. to obtain a readily stirred slurry. The reaction mixture was held at 155-165° C. for four hours. The reaction mixture was cooled to about 50° C. and quenched by slowly adding ice cold diluted hydrochloric acid (200 ml of 5percent HCl) to the reactor. The suspension thus obtained was heated to 50° C. and a red-violet solid was collected by filtration. The red-violet solid was slurried at 50° C. in water (100 ml) to remove the salts from the compound, and the solid was collected by filtration, washed with water (30 ml) and dried in an oven at 50° C. overnight to yield a red-violet complex of 7-HQ with AlCl3 (27.1 g), containing about 2percent of 5-HQ. The complex (27.1 g) was dissolved in methanol (220 ml) while heating under reflux and 47percent aqueous sodium hydroxide solution was added to produce a pH of about 7. The hot solution was filtered and activated carbon (0.8 g) was added to the filtrate. The mixture was heated under reflux for half an hour and the activated carbon was collected by filtration. Methanol (about 190 ml) was removed from the filtrate by evaporation and water (30 ml) was added to the residue thus obtained. The mixture was stirred at ambient temperature for half an hour and the colorless crystals were collected by filtration, washed with a cold methanol-water (1:1) mixture (20 ml) and dried at 50° C. overnight to yield 7-hydroxy-3,4-dihydro-2(1H)-quinolinone (18.8 g, 62.3percent yield, having a purity of 99.4percent by HPLC). |
61.3% | Stage #1: With N,N-dimethyl acetamide In water at 95 - 165℃; for 5.5 h; Stage #2: With methanol; sodium hydroxide In water at 20℃; for 1 h; Heating / reflux |
Example 1; Preparation of 7-HQ in a Mixture Containing a High Boiling Solvent; A 3.0 l reactor was charged with 3-MPCA (300 g, 1.4 mole), AlCl3 (920 g, 7.0 mole, 5 eq.) and N,N-dimethylacetamide (65 ml, 61 g, 0.5 eq.) and the reaction mixture was heated under stirring to about 160° C. to obtain a readily stirred liquid. The reaction mixture was held at 155-165° C. for about four hours under stirring, then cooled to about 50° C. Cold water (1500 ml) was added for a time period of half an hour and the mixture was stirred under heating to about 95° C. for one hour. The suspension thus obtained was cooled to about 50° C. and a red-violet solid was collected by filtration, washed with water (400 ml) and dried in an oven at 50° C. overnight to yield a red-violet complex of 7-HQ with AlCl3 (202 g), containing about 2percent of 5-HQ. The complex (202 g) was dissolved in methanol (1600 ml) while heating under reflux and 47percent aqueous sodium hydroxide solution was added to produce a pH of about 7. The hot solution was filtered and activated carbon (6 g) was added to the filtrate. The mixture was heated under reflux for half an hour and the activated carbon was collected by filtration. Methanol (about 1400 ml) was removed from the filtrate by evaporation and water (200 ml) was added to the residue thus obtained. The mixture was stirred at ambient temperature for half an hour and the colorless crystals were collected by filtration, washed with a cold methanol-water (1:1) mixture (10 ml) and dried at 50° C. overnight to yield 7-hydroxy-3,4-dihydro-2(1H)-quinolinone (140.5 g, 61.3percent yield, having a purity of 99.3percent by HPLC). Re-crystallization from methanol gave colorless crystals: mp 230-231.5° C. |
61.3% | Stage #1: at 95 - 165℃; for 5.5 h; Stage #2: With methanol; sodium hydroxide In water at 20℃; for 1 h; Heating / reflux |
Example 3; Preparation of 7-HQ in a Melt; A 2.0 l reactor was charged with 3-MPCA (150 g, 0.69 mole) and AlCl3 (460 g, 3.45 mole, 5 eq.).The reaction mixture was heated under stirring to about 160° C. to obtain a liquid. The reaction mixture was stirred and held at 155-165° C. for about four hours. Stirring was stopped and the reaction mixture was cooled to 50° C. Ice cold diluted hydrochloric acid (750 ml of 5percent HCl) was added to the reactor during half an hour and the mixture was stirred while heating to about 95° C. for one hour. The suspension thus obtained was cooled to about 50° C. and a red-violet solid was collected by filtration, washed with water (200 ml) and dried in an oven at 50° C. overnight to yield the red-violet complex of 7-HQ with AlCl3 (100 g), containing about 2percent of 5-HQ. The complex (100 g) was dissolved in methanol (800 ml) while heating under reflux and 47percent aqueous sodium hydroxide solution was added to produce a pH of about 7. The hot solution was filtered and activated carbon (3 g) was added to the filtrate. The mixture was heated under reflux for half an hour and the activated carbon was collected by filtration. Methanol (about 700 ml) was removed from the filtrate by evaporation and water (100 ml) was added to the residue thus obtained. The mixture was stirred at ambient temperature for half an hour and the colorless crystals were collected by filtration, washed with a cold methanol-water (1:1) mixture (50 ml) and dried at 50° C. overnight to yield 7-hydroxy-3,4-dihydro-2(1H)-quinolinone (70.2 g, 61.3percent yield, having a purity of 99.5percentby HPLC). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium hydroxide; In propan-1-ol; | (A) 5-(2-chloroethoxy)-3,4-dihydrocarbostyril Potassium hydroxide (20 g) was added to a solution of 3,4-dihydro-<strong>[30389-33-4]5-hydroxycarbostyril</strong> (32.5 g) in propanol (250 mL), and stirred at 50-60 C. until complete dissolution. 1-bromo-2-chloroethane (30 g) was then added, and the mixture heated at reflux temperature for 15 hours. After cooling, the reaction mixture was poured into aqueous sodium hydroxide (2N, 500 mL). The crude product thus formed was isolated by filtration, then recrystallized from diisopropyl ether to yield 31 g of pure 5-(2-chloroethoxy)-3,4-dihydrocarbostyril. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62.3% | Example 2; Preparation of 7-HQ in the Presence of a Salt; A 0.5 l reactor was charged with 3-MPCA (40 g, 0.185 mole), AlCl3 (125 g, 0.925 mole, 5 eq.) and anhydrous sodium chloride (20 g) and the reaction mixture was heated under stirring to about 160 C. to obtain a readily stirred slurry. The reaction mixture was held at 155-165 C. for four hours. The reaction mixture was cooled to about 50 C. and quenched by slowly adding ice cold diluted hydrochloric acid (200 ml of 5% HCl) to the reactor. The suspension thus obtained was heated to 50 C. and a red-violet solid was collected by filtration. The red-violet solid was slurried at 50 C. in water (100 ml) to remove the salts from the compound, and the solid was collected by filtration, washed with water (30 ml) and dried in an oven at 50 C. overnight to yield a red-violet complex of 7-HQ with AlCl3 (27.1 g), containing about 2% of 5-HQ. The complex (27.1 g) was dissolved in methanol (220 ml) while heating under reflux and 47% aqueous sodium hydroxide solution was added to produce a pH of about 7. The hot solution was filtered and activated carbon (0.8 g) was added to the filtrate. The mixture was heated under reflux for half an hour and the activated carbon was collected by filtration. Methanol (about 190 ml) was removed from the filtrate by evaporation and water (30 ml) was added to the residue thus obtained. The mixture was stirred at ambient temperature for half an hour and the colorless crystals were collected by filtration, washed with a cold methanol-water (1:1) mixture (20 ml) and dried at 50 C. overnight to yield 7-hydroxy-3,4-dihydro-2(1H)-quinolinone (18.8 g, 62.3% yield, having a purity of 99.4% by HPLC). | |
61.3% | Example 1; Preparation of 7-HQ in a Mixture Containing a High Boiling Solvent; A 3.0 l reactor was charged with 3-MPCA (300 g, 1.4 mole), AlCl3 (920 g, 7.0 mole, 5 eq.) and N,N-dimethylacetamide (65 ml, 61 g, 0.5 eq.) and the reaction mixture was heated under stirring to about 160 C. to obtain a readily stirred liquid. The reaction mixture was held at 155-165 C. for about four hours under stirring, then cooled to about 50 C. Cold water (1500 ml) was added for a time period of half an hour and the mixture was stirred under heating to about 95 C. for one hour. The suspension thus obtained was cooled to about 50 C. and a red-violet solid was collected by filtration, washed with water (400 ml) and dried in an oven at 50 C. overnight to yield a red-violet complex of 7-HQ with AlCl3 (202 g), containing about 2% of 5-HQ. The complex (202 g) was dissolved in methanol (1600 ml) while heating under reflux and 47% aqueous sodium hydroxide solution was added to produce a pH of about 7. The hot solution was filtered and activated carbon (6 g) was added to the filtrate. The mixture was heated under reflux for half an hour and the activated carbon was collected by filtration. Methanol (about 1400 ml) was removed from the filtrate by evaporation and water (200 ml) was added to the residue thus obtained. The mixture was stirred at ambient temperature for half an hour and the colorless crystals were collected by filtration, washed with a cold methanol-water (1:1) mixture (10 ml) and dried at 50 C. overnight to yield 7-hydroxy-3,4-dihydro-2(1H)-quinolinone (140.5 g, 61.3% yield, having a purity of 99.3% by HPLC). Re-crystallization from methanol gave colorless crystals: mp 230-231.5 C. | |
61.3% | Example 3; Preparation of 7-HQ in a Melt; A 2.0 l reactor was charged with 3-MPCA (150 g, 0.69 mole) and AlCl3 (460 g, 3.45 mole, 5 eq.).The reaction mixture was heated under stirring to about 160 C. to obtain a liquid. The reaction mixture was stirred and held at 155-165 C. for about four hours. Stirring was stopped and the reaction mixture was cooled to 50 C. Ice cold diluted hydrochloric acid (750 ml of 5% HCl) was added to the reactor during half an hour and the mixture was stirred while heating to about 95 C. for one hour. The suspension thus obtained was cooled to about 50 C. and a red-violet solid was collected by filtration, washed with water (200 ml) and dried in an oven at 50 C. overnight to yield the red-violet complex of 7-HQ with AlCl3 (100 g), containing about 2% of 5-HQ. The complex (100 g) was dissolved in methanol (800 ml) while heating under reflux and 47% aqueous sodium hydroxide solution was added to produce a pH of about 7. The hot solution was filtered and activated carbon (3 g) was added to the filtrate. The mixture was heated under reflux for half an hour and the activated carbon was collected by filtration. Methanol (about 700 ml) was removed from the filtrate by evaporation and water (100 ml) was added to the residue thus obtained. The mixture was stirred at ambient temperature for half an hour and the colorless crystals were collected by filtration, washed with a cold methanol-water (1:1) mixture (50 ml) and dried at 50 C. overnight to yield 7-hydroxy-3,4-dihydro-2(1H)-quinolinone (70.2 g, 61.3% yield, having a purity of 99.5%by HPLC). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
PREPARATION 72 5-(2,3-Epoxypropoxy)-2-hydroxy-3,4-dihydroquinoline The title compound was prepared according to the method of Preparation 71 but using 3,4-dihydro-<strong>[30389-33-4]5-hydroxycarbostyril</strong> instead of 1,5-dihydroxy-3,4-dihydroisoquinoline. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With pyridine; In dichloromethane; at 0℃; for 2h; | Pyridine (30 ml) and trifluoromethanesulfonic anhydride (25 g) were added with stirring at 00C to an anhydrous dichloromethane solution (200 ml) of 5-hydroxy-3,4-dihydro-IH- quinolin-2-one (15.9 g) , followed by stirr+/-ng for 2 hours. The resulting mixture was concentrated under reduced pressure, water was added to the residue, and extraction w+/-th dichloromethane was performed. The extract was washed with water, an aqueous potassium hydrogensulfate solution and water in this order, and dried over anhydrous sodium sulfate. After concentration under reduced pressure, the residue was recrystallized from an ethyl acetate-diisopropyl ether mixed solvent to thereby obtain 28 g (yield: 97%) of 5-trifluoromethanesulfonylochiy-3,4-dihydro-lH- quinolin-2-one as a light brown powder. EPO <DP n="199"/>1H-NMR(CDCl3) dppm:2.67 (2H, dd, J=6. 3Hz , J=8.8Hz ) , 3.07 ( 2H, t, J=7.2Hz ) , 6.80-6.90( lH,m) , 6.90-7.02 ( lH,m) , 7. 16-7.32 ( IH, m) , 8.95( lH,brs) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With 1H-imidazole; In N,N-dimethyl-formamide; at 20℃; for 4h; | Description 81; 5-ff(1.1-Dimethvlethvnfdimethvnsilvnoxv>-3.4-dihvdro-2f 1HVquinolinone (D81); To a stirred solution of 5-hydroxy-3,4-dihydro-2(1H)-quinolinone (640 mg, 3.93 mmol)in DMF (3.5 ml) were added t-butyldimethylsilyl chloride (651 mg, 4.32 mmol) andimidazole (321 mg, 4.71 mmol) at room temperature. After 4 hours water (10 ml) wasadded and the mixture was extracted with DCM (3 x 70 ml). The combined organiclayers were dried (Na2SO4), concentrated in vacua to give the title compound (997mg, 91 %) that was used in the next step without further purification; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With triethylamine; In acetonitrile; at 0 - 20℃; for 15h; | Description 71; 2-Oxo-1.2.3.4-tetrahvdro-5-quinolinvl trifluoromethanesulfonate (D71); 1,1,1-Trifluoro-A/-phenyl-A/-[(trifluoromethyl)sulfonyl]methanesulfonamide (1.21 g,3.39 mmol) was added portion-wise to a stirred suspension of 5-hydroxy-3,4-dihydro-2(1H)-quinolinone (Davos, commercially available) (460 mg, 2.82 mmol) in CH3CN(25 ml), and triethylamine (492 ul, 3.53 mmol) at 0C. The reaction mixture wasstirred for 15 hours at room temperature then quenched with water (20 ml) andextracted with DCM (3 x 50 ml). The combined organic layers were dried (Na2SO4)and concentrated in vacuo. The crude product was purified by SPE-SI cartridge,eluting with cyclohexane/ethyl acetate (7:3), to afford the title compound (812 mg,97%); |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With formaldehyd; In water; | (A) 8-diethylaminomethyl-3,4-dihydro-<strong>[30389-33-4]5-hydroxycarbostyril</strong> To a stirred suspension of 3,4-dihydro-<strong>[30389-33-4]5-hydroxycarbostyril</strong> (30 g, 184 mM) in water (300 mL) was added diethylamine (14 g, 191 mM) followed by a 36% solution of formaldehyde in water (300 mL). The mixture was stirred for 5 hours and the resulting precipitate was filtered and washed with ice-water (50 mL) to give 8-diethylaminomethyl-3,4-dihydro-<strong>[30389-33-4]5-hydroxycarbostyril</strong>. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In methanol; water; | REFERENCE EXAMPLE 1 4.2 Grams of potassium hydroxide were dissolved in 200 ml of methanol, then 10 g of 5-hydroxy-3,4-dihydrocarbostyril were added thereto. Next, 10 g of 2-bromoethanol were added dropwise thereto under refluxing conditions. The reaction mixture was further refluxed for 4 hours, then was concentrated. To the residue thus obtained was added water, and the insoluble matter was collected by filtration, and was washed with water, then recrystallized from methanol to yield 2.1 g of 5-(2-hydroxyethoxy)-3,4-dihydrocarbostyril in the form of colorless needle-like crystals. Melting point: 176-178 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethanol; | EXAMPLE 1 Preparation of Compound of Formula II 1.53 g of 5-hydroxy-3,4-dihydrocarbostyril and 3.5 g of epichlorohydrin were added to 30 ml of a methanolic solution of 0.216 g of sodium metal and the resulting solution was stirred at a temperature of from 55 to 60 C. for 4 hours. After allowing the solution to cool, the precipitated sodium chloride was filtered and the filtrate was concentrated to dryness under reduced pressure. To the resulting residue was added acetone to crystallize the product. Recrystallization of the product from ethanol gave 0.8 g of 5-(2,3-epoxy)propoxy-3,4-dihydrocarbostyril having a melting point of 172-173 C. as a colorless amorphous solid. A solution of the filtrate in acetone was concentrated to dryness and the resulting residue was recrystallized from ethyl acetate to give 0.05 g of 5-(2-hydroxy-3-chloro)propoxy-3,4-dihydrocarbostyril having a melting point of 157-158 C. as a colorless amorphous solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydroxide; In water; | EXAMPLE 2 Preparation of Compound of Formula II To a solution of 0.6 g of sodium hydroxide dissolved in 40 ml of water were added 2.5 g of 5-hydroxy-3,4-dihydrocarbostyril and 3.0 g of epibromohydrin, and the resulting solution was stirred at a temperature of from 60 to 65 C. for 4 hours. After allowing the solution to cool, the precipitated crystals were separated by filtration and recrystallized from ethanol to give 1.9 g of 5-(2,3-epoxy)propoxy-3,4-dihydrocarbostyril having a melting point of 172-173 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With chlorine; In water; acetic acid; | REFERENCE EXAMPLE 2 16.4 Grams of 5-hydroxy-3,4-dihydrocarbostyril are dissolved in 300 ml of acetic acid. This solution is stirred at room temperature, and 50 ml of acetic acid solution containing 7 g of chlorine are added dropwise and the reaction is continued for 3 hours with stirring The reaction mixture is poured into 500 ml of water and allowed to stand for 1 hour and the precipitate thus formed is separated by filtration, washed with water and then dried. Recrystallization from ethanolwater obtains 13.5 g of 6-chloro-5-hydroxy-3,4-dihydrocarbostyril in the form of colorless needle-like crystals with a melting point of 209-210 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With chlorine; In 6-chloro-5-hydroxy-3,4-dihydrocarbostyril; acetic acid; | REFERENCE EXAMPLE 3 16.4 Grams of 5-hydroxy-3,4-dihydrocarbostyril are dissolved in 300 ml of acetic acid. This solution is stirred at room temperature, and 80 ml of acetic acid solution containing 16.4 g of chlorine are added dropwise and the reaction is continued for 3 hours with stirring. Similar to the procedure mentioned in REFERENCE EXAMPLE 2, the crude crystals are recrystallized from methanol to obtain 16 g of 6,8-dichloro-5-hydroxy-3,4-dihydrocarbostyril in the form of colorless needle-like crystals with a melting point of 259-260 C. | |
With sulfuryl dichloride; In chloroform; acetic acid; | REFERENCE EXAMPLE 1 24 Grams of 5-hydroxy-3,4-dihydrocarbostyril is suspended in 200 ml of acetic acid and 300 ml of chloroform. This suspension is adjusted to 40 to 50 C., and then 36 ml of sulfuryl chloride is added dropwise thereto under agitation, followed by one-hour agitation at the same temperature. The reaction solution is poured into ice-water and the precipitate is filtered out. This product is recrystallized from methanol to obtain 20 gr of 5-hydroxy-6,8-dichloro-3,4-dihydrocarbostyril in the form of colorless plate-like crystals with melting point of 246-248 C. | |
With chlorine; In water; acetic acid; | REFERENCE EXAMPLE 3 16.4 Grams of 5-hydroxy-3,4-dihydrocarbostyril was dissolved in 300 ml of acetic acid, and under stirring condition at a room temperature 80 ml of acetic acid containing 14 g chlorine was added dropwise and the reaction was continued for 3 hours under stirring. The reaction mixture was poured into 500 ml of water and allowed to stand for 1 hour. The precipitates thus formed were obtained by filtration, and washed with water, dried and recrystallized from methanol. 16 Grams of 6,8-dichloro-5-hydroxy-3,4-dihydrocarbostyril was obtained as in the form of colorless needle-like crystals. Melting point: 259-260 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium hydroxide; In N-methyl-acetamide; methanol; benzene; | REFERENCE EXAMPLE 19 10 g of 5-hydroxy-3,4-dihydrocarbostyril was added to 100 ml of methanol having dissolved therein 3.8 g of potassium hydroxide and the mixture was stirred at room temperature for 30 minutes followed by removing methanol under reduced pressure. Benzene was added to the residue to form crystals and then benzene was removed by evaporation. The residue thus-obtained was suspended in 50 ml of dimethylformamide and 10.6 g of methanesulfonyl chloride was added dropwise to the suspension while ice-cooling with stirring. After adding 3.5 g of methanesulfonyl chloride, the resulting mixture was stirred at room temperature for 4 hours. After the completion of the reaction, the solvent was removed under reduced pressure and the residue was purified through a silica gel column chromatography (silica gel:Wako C-200, a trade name for a product of Wako Junyaku Co., Ltd.; eluant:chloroform). Recrystallization of the elude from water-containing ethanol gave 5.7 g of 5-methanesulfonyloxy-3,4-dihydrocarbostyril as colorless prismatic crystals having a melting point of 227 to 231 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium hydroxide; In N-methyl-acetamide; methanol; benzene; | REFERENCE EXAMPLE 1 10 g of 5-hydroxy-3,4-dihydrocarbostyril was added to 100 ml of methanol having dissolved therein 3.8 g of potassium hydroxide and the mixture was stirred at room temperature for 30 minutes followed by removing methanol under reduced pressure. Benzene was added to the residue to form crystals and then benzene was removed by evaporation. The residue thus-obtained was suspended in 50 ml of dimethylformamide and 10.6 g of methanesulfonyl chloride was added dropwise to the suspension while ice-cooling with stirring. After adding 3.5 g of methanesulfonyl chloride the resulting mixture was stirred at room temperature for 4 hours. After the completion of the reaction, the solvent was removed under reduced pressure and the residue was purified through silica gel column chromatography (silica gel: Wako C-200, a trade name for a product of Wako Junyaku Co., Ltd.; eluent: chloroform). Recrystallization of the elute from water-containing ethanol gave 5.7 g of 5-methanesulfonyloxy-3,4-dihydrocarbostyril as colorless prismatic crystals having a melting point of 227 to 231 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | EXAMPLE 81 5-(4-Phenylsulfonyl-butoxy)-3,4-dihydro-carbostyril Prepared analogous to Example 4 from 5-hydroxy-3,4-dihydro-carbostyril and 4-phenylsulfonyl-butyl bromide. M.p.: 187-189 C. Yield: 73% of theory. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64% | EXAMPLE 80 5-(4-Phenylsulfinyl-butoxy)-3,4-dihydro-carbostyril Prepared analogous to Example 4 from 5-hydroxy-3,4-dihydro-carbostyril and 4-phenylsulfinyl-butyl bromide. M.p.: 136-138 C. Yield: 64% of theory. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64% | EXAMPLE 79 5-(4-Phenylmercapto-butoxy)-3,4-dihydro-carbostyril Prepared analogous to Example 4 from 5-hydroxy-3,4-dihydro-carbostyril and 4-phenylmercapto-butyl bromide. M.p.: 155-157 C. Yield: 64% of theory. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium hydroxide; In isopropyl alcohol; | REFERENCE EXAMPLE 6 16.3 Grams of 5-hydroxy-3,4-dihydrocarbostyril and 9 g of potassium hydroxide were mixed with 150 ml of isopropanol and stirred at 70-80 C. for 30 minutes. Next, 25 g of 1,3-bromochloropropane was added thereinto and heated under refluxing condition for 6 hours. After the reaction was completed, the reaction mixture was poured into 200 ml of 2N-sodium hydroxide aqueous solution and the insoluble matters thus formed were obtained by filtration, washed with water and dried. Crude crystals thus obtained were recrystallized from ethanol to obtain 18.5 g of 5-(3-chloropropoxy)-3,4-dihydrocarbostyril as in the form of colorless needle-like crystals. Melting point: 176-178 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63.6% | Hydroxy-3,4-dihydro-2 (1H) -quinolone (0.015 mol) was dissolved in a 0.2 mol / L sodium hydroxide solution (the amount of sodium hydroxide was 5-hydroxy- - dihydro-2 (1H) -quinolone 0.5 molar times), stirred 10min, was added epichlorohydrin (0.03mol), 55 ~ 60 C the reaction was stirred for about 4h, resulting in a large amount of white floc, TLC test After the reaction was completed, the solution was cooled to room temperature, ethyl acetate was added (its amount was 1 time the volume of the reaction solution), the sub-water was removed by a separatory funnel, filtered, and the filter cake was recrystallized from acetone to give the white powdery solid 5- , 3-glycidyloxy) -3,4-dihydro-2 (1H) -quinolone (yield 63.6%), | |
With sodium hydroxide; In methanol; | REFERENCE EXAMPLE 5 16.4 Grams of 5-hydroxy-3,4-dihydrocarbostyril and 3.7 g of sodium hydroxide were added into 100 ml of methanol and stirred at 40-50 C. for 3 hours, then 150 ml of epichlorohydrin was added thereto and heated under refluxing condition for 5 hours. The reaction mixture was concentrated under a reduced pressure to dryness and the residue thus obtained was recrystallized from methanol-water (1:1) to obtain 18.5 g of 5-(2,3-epoxypropoxy)-3,4-dihydrocarbostyril having the melting of 172-173 C. as in the form of coloress amorphous crystals. | |
With NaH; In N,N-dimethyl-formamide; | Nmr and mass spectra confirmed the structures of both the products (A) and (B). The compound, 5-(2,3-Epoxy)-propoxy-3,4-dihydrocarbostyril was prepared as follows: Dry 5-hydroxy-3,4-dihydrocarbostyril (20.0 g., 0.122 mole); Y. Tamura et al, Chem. Ind., 1435 (1970) was added with stirring to a suspension of 50% NaH dispersion (6.14 g., 0.128 mole) in dry DMF (110 ml) under N2. This was followed by a portionwise addition of epichlorohydrin (33.8 g., 0.366 mole) at 30 C. After the initial reaction was over, the mixture was heated at 65 for 2 hours, stirred overnight at room temperature, filtered and the filterate was concentrated in vacuo. When solid started to separate, the mixture was diluted with absolute ethanol and filtered to give 10.5 g. (m.p. 164-68) of the product which was 96% pure (TLC). The alcoholic filtrate was concentrated, the gummy residue washed several times with water, covered with ethanol and filtered to give 0.6 g. of the same material. Total yield 11.1 g. (42%). The product was identical to the one prepared by the method reported by K. Nakagawa et al, J. Med. Chem., 17, 529 (1974). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethanol; | EXAMPLE 5 0.23 g of sodium metal was dissolved in 40 ml of ethanol, and 1.63 g of 5-hydroxy-3,4-dihydrocarbostyril and 1.1 g of glycerol alpha-monochlorohydrin were added to the resulting solution followed by refluxing the mixture for 6 hours. After allowing the mixture to cool, the precipitated crystals were filtered, and the filtrate was concentrated to dryness. The residue thus obtained was extracted with 100 ml of chloroform, and the extract was washed with a 5% aqueous sodium hydroxide solution and then water and then dried over anhydrous sodium sulfate. The chloroform was then removed by distillation and the resulting residue was recrystallized from ethanol to give 0.7 g of 5-(2,3-dihyroxy)propoxy-3,4-dihydrocarbostyril as a colorless amorphous solid having a melting point of 173 - 175 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium iodide; sodium ethanolate; In ethanol; | REFERENTIAL EXAMPLE 6 To 200 ml. of ethanol were added 32 g. of 5-hydroxy-3,4-dihydrocarbostyril, 17 g. of sodium ethylate and 1 g. of potassium iodide, and the resulting mixture was refluxed with stirring for 1 hour to form a solution. Into this solution was dropped 56 g. of 1,6-dibromohexane, and the resulting mixture was refluxed with stirring for 12 hours. After the reaction, the reaction liquid was cooled to deposit crystals. The deposited crystals were recovered by filtration, washed with a 0.5N-aqueous sodium hydroxide solution and water in this order, and then recrystallized from ethanol to obtain 40 g. of 5-(6'-bromo)hexyloxy-3,4-dihydrocarbostyril in the form of colorless needle-like crystals, m.p. 135-136 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In methanol; acrylonitrile; | REFERENTIAL EXAMPLE 9 A suspension of 11.4 g. of 5-hydroxy-3,4-dihydrocarbostyril in 37.1 g. of acrylonitrile was charged with 2 ml. of a 40% methanol solution of Triton B, and refluxed for 8.5 hours. The reaction liquid was cooled to deposit crystals, which were then recovered by filtration and recrystallized from methanol to obtain 6.5 g. of 5-(2'-cyanoethoxy)-3,4-dihydrocarbostyril in the form of colorless needle-like crystals, m.p. 217-222.5 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
General procedure: A solution of 6-hydroxy-3,4-dihydrocarbostyril (corresponding to 44) (2.00g, 12.26mmol) in DMF (10ml) was added dropwise to a suspension of NaH (60% in mineral oil, 0.59g, 14.71mmol) in DMF (5ml) for 14min at 0C with a CaCl2 tube. After stirring for 20min at 0C, a solution of 6-bromohexanoic acid ethyl ester (3.06g, 13.48mmol) in DMF (7ml) was added dropwise to the reaction mixture for 7min at 0C. The reaction mixture was stirred overnight, during which time the ice was allowed to gradually melt and was subsequently stirred for 3h at 110C. After cooling, H2O (100ml) was added to the mixture, and the resulting mixture was extracted with AcOEt (100ml×3). The combined organic layer was washed with H2O (100ml×1) and brine (100ml×1), dried over Na2SO4 (anhyd), filtered, and concentrated under reduced pressure. The crude product was purified through open silica gel column chromatography (n-hexane/AcOEt=1:2) to afford a colorless solid (2.56g, 8.38mmol, y. 68%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With boron tribromide; caesium carbonate; In acetonitrile; for 4h;Reflux; | To a stirred solution of 5-hydroxy-3,4-dihydroquinolin-2(lH)-one 1 (2 g, 12.27 mmol) in acetonitrile (80 mL) at RT, were added Cs2C03 (6 g, 18.4 mmol) and benzyl bromide (1.46 mL, 12.27 mmol). The mixture was heated to reflux for 4 h. After cooling to RT, the mixture was diluted with water (50 mL) and stirred for 20 min. The precipitated solid was collected via filtration, washed with water (15 mL) and dried under vacuum to afford compound 2 (2.5 g, 81%) as an off white solid. 1H MR (500MHz, DMSO-i): delta 10.05 (s, 1H), 7.44 - 7.47 (m, 2H), 7.40 (m, 2H), 7.33 (m, 1H), 7.08 (m, 1H), 6.70 (m, 1H), 6.49 (m, 1H), 5.10 (s, 2H), 2.84 (m, 2H), 2.41 (m, 2H); LCMS Mass: 254.0 (M++l). |
81% | With caesium carbonate; In acetonitrile; for 4h;Inert atmosphere; Reflux; | To a stirred solution of 5-hydroxy-3,4-dihydroquinolin-2(1I])-one 1 (2 g, 12.27 mmol) in acetonitrile (80 mL) were added benzyl bromide (1.46 mL, 12.27 mmol) and Cs2CO3 (6 g, 18.4 mmol) at RT under inert atmosphere. The reaction mixture was heated to reflux temperature and stirred for 4 h. The reaction mixture was cooled to RT then diluted with water (80 mL) and stirred vigorously for 10 mm. The obtained solid was filtered, washed with water and dried under vacuum to afford compound 2 (2.5 g, 81%) as an off white solid. ?H NIVIR (500 MHz, DMSOd 6): 10.05 (s, 1H), 7.45 (d, J= 6.9 Hz 2H), 7.40 (t, J= 7.5 Hz, 2H), 7.35-7.30 (m, 1H), 7.08 (t, J= 8.1 Hz, 1H), 6.70 (d, J= 8.4 Hz, 1H), 6.49 (d, J 7.8 Hz, 1H), 5.10 (s, 2H), 2.84 (t, J 7.7 Hz, 2H), 2.41 (t, J= 7.7 Hz, 2H); LCMS Mass: 254.0 (M+1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
49% | With potassium carbonate; In 1-methyl-pyrrolidin-2-one; at 20℃; for 3h; | To a stirred solution of 5-hydroxy-3,4-dihydroquinolin-2(lH)-one 1 (50 mg, 0.31 mmol) in N-methyl-2-pyrrolidone (3 mL) at RT, were added 2-chloro-6- (trifluoromethyl)isonicotinonitrile (63 mg, 0.31 mmol) and K2C03 (85 mg, 0.61 mmol). The mixture was stirred at RT for 3 h. The mixture was diluted with water (10 mL) and extracted with EtOAC (2 x 15 mL). The combined organic extracts were washed with brine (10 mL), dried (Na2S04), filtered, and concentrated under reduced pressure. The crude was triturated with Et20 (2 x 5 mL) to afford compound 2 (50 mg, 49percent) as white solid. 1H NMR (400 MHz, OMSO-d6): delta 10.28 (s, 1H), 8.18 (s, 1H), 7.97 (s, 1H), 7.23 (t, J= 8.0 Hz, 1H), 6.85-6.78 (m, 2H), 2.65 (t, J = 7.6 Hz, 2H), 2.42-2.35 (m, 2H); LC-MS (ESI): m/z 332.1 (M - 1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92.7% | With N-Bromosuccinimide; In cyclohexane; for 3.0h;Cooling with ice; Reflux; | To a 100 ml three-necked flask were added 3,4,7,8-tetrahydro-2,5 (1 H, 6Eta) -quinoline dione (0.02 mol) and cyclohexane (25 ml) After stirring to dissolve in the ice bath for 10min, slowly add dropwise a solution of N-bromosuccinimide (0.03mol) in cyclohexane (5ml), and reflux for 3h at the end of the dropwise addition. After completion of the reaction by TLC, cool down to room temperature . Water was added (amount was 0.7 times the volume of the reactant), and the mixture was allowed to stand with stirring. The aqueous layer was extracted with ethyl acetate (1 × the volume of the aqueous layer 4 times), and the organic layers were combined. Anhydrous sulfuric acid Calcium was dried and filtered, the filtrate was evaporated to remove the solvent, and the residue was dried to give an off-white solid as a 5-hydroxy-Dihydro-2 (1H) -quinolone (Yield 92.7%), mp 233 ~ 234 C, BP2013-HPLC method chromatography purity 94.3%. |
Tags: 30389-33-4 synthesis path| 30389-33-4 SDS| 30389-33-4 COA| 30389-33-4 purity| 30389-33-4 application| 30389-33-4 NMR| 30389-33-4 COA| 30389-33-4 structure
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