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Product Details of [ 30389-33-4 ]

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 :

Safety of [ 30389-33-4 ]

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:

Application In Synthesis of [ 30389-33-4 ]

* 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.

  • Upstream synthesis route of [ 30389-33-4 ]
  • Downstream synthetic route of [ 30389-33-4 ]

[ 30389-33-4 ] Synthesis Path-Upstream   1~5

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Reference: [1] Journal of Organic Chemistry, 1981, vol. 46, # 18, p. 3719
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YieldReaction ConditionsOperation 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.
Reference: [1] Patent: CN107337639, 2017, A, . Location in patent: Paragraph 0120; 0127; 0139; 0150; 0161; 0171; 0172; 0183
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YieldReaction ConditionsOperation 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).
Reference: [1] Patent: US2006/79690, 2006, A1, . Location in patent: Page/Page column 6
[2] Patent: US2006/79690, 2006, A1, . Location in patent: Page/Page column 5-6
[3] Patent: US2006/79690, 2006, A1, . Location in patent: Page/Page column 6
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Reference: [1] Journal of Organic Chemistry, 1981, vol. 46, # 18, p. 3719
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Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 23, p. 7092 - 7096
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