* 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.
Reference：
[1] Journal of Organic Chemistry, 1981, vol. 46, # 18, p. 3719
2
[ 5057-12-5 ]
[ 31570-97-5 ]
[ 30389-33-4 ]
Reference：
[1] Journal of Organic Chemistry, 1981, vol. 46, # 18, p. 3719
3
[ 5057-12-5 ]
[ 30389-33-4 ]
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.
Reference：
[1] Patent: CN107337639, 2017, A, . Location in patent: Paragraph 0120; 0127; 0139; 0150; 0161; 0171; 0172; 0183
4
[ 5057-12-5 ]
[ 31570-97-5 ]
[ 30389-33-4 ]
Reference：
[1] Journal of Organic Chemistry, 1981, vol. 46, # 18, p. 3719
5
[ 504-02-9 ]
[ 79-10-7 ]
[ 5057-12-5 ]
Yield
Reaction Conditions
Operation in experiment
92%
at 80℃; for 5 h; Inert atmosphere
General procedure: 1,3-Dicarbonyls (8.9 mmol, 1 equiv.) followed by ammonium acetate (10.6 mmol, 1.2 mmol, 1.2 equiv.) were added to the solution of acrylic acid (10.6 mmol, 1.2 equiv.). The reactant mass was mixed thoroughly with a spatula and heated at 80 °C with stirring under a nitrogen atmosphere for 5 h. After cooling, the reaction mixture was diluted with 10mL distilled water and extracted twice with ethyl acetate (210 mL). The organic extracts were dried over anhydrous Na2SO4. After filtration, the solvent was evaporated under reduced pressure and subjected to column chromatography (ethyl acetate=hexane) to obtain pure products. The characterization data of the compounds are given.
-amino-2-cyclohexenone (0.02mol) and acrylic acid (0.024mol) was added to a 100ml three-necked flask, heated to reflux with stirring 6h, cooled to room temperature, the reaction solution was solidified to give a reddish brown solid , Adding absolute ethanol (5ml), heating and dissolving, cooling to room temperature, filtering and drying the filter cake to obtain light yellow crystal which is 3,4,7,8-tetrahydro-2,5 (1H, 6H) Ketone (yield 90.2percent),
Reference：
[1] Journal of Organic Chemistry, 1981, vol. 46, # 18, p. 3719
[2] Patent: CN107337639, 2017, A, . Location in patent: Paragraph 0120; 0125; 0137; 0148; 0159; 0169; 0170; 0181
[3] Patent: US5068334, 1991, A,
With palladium 10% on activated carbon; potassium hydroxide; In methanol; water; at 25.0℃; under 2068.65 Torr; for 2.0h;
White solid. This compound was prepared(Witiak et al., 1986) by a solution of <strong>[5057-12-5]hexahydroquinoline-2,5-dione</strong> (2) (1.0 g, 6.1 mmol), 10 % aqueous KOH (1.5 mL), and MeOH (50 mL) was hydrogenated over350 mg of 10 % Pd/C at room temperature (25 C) and 40psi for 2 h. The solution was acidified to pH 2 with 10 %HCl solution, filtered and concentrated to give solidproduct. The product was dissolved in DCM (50 mL) andpassed through a small plug of Celite, and the filtrate driedwith sodium sulfate was evaporated under reduced pressureto give a mixture (1:2) of trans and cis diastereoisomers,respectively (4), as a white solid 0.75 g (74 %); 1H-NMR(CDCl3, 400 MHz,) delta: 7.5 (brs, 1H, NH), 7.3 (brs, 1H,NH), 4.0-3.9 (m, 1H), 3.2-3.1 (m, 1H), 2.5-1.4 (m, 22H).
-amino-2-cyclohexenone (0.02mol) and acrylic acid (0.024mol) was added to a 100ml three-necked flask, heated to reflux with stirring 6h, cooled to room temperature, the reaction solution was solidified to give a reddish brown solid , Adding absolute ethanol (5ml), heating and dissolving, cooling to room temperature, filtering and drying the filter cake to obtain light yellow crystal which is 3,4,7,8-tetrahydro-2,5 (1H, 6H) Ketone (yield 90.2%),
45.1%
In methanol;
EXAMPLE G 3,4,7,8-Tetrahydro-2,5(1H,6H)-quinolinedione 5.00 g (0.675 mol) of 1-amino-cyclohexen-3-one and 65.65 g (1.35*0.675 mol) of acrylic acid are stirred for 3 hours under nitrogen in an oil bath heated to 180 C. The mixture is cooled and recrystallized from 1000 ml of methanol. Melting point: 192-194.5 C., Yield: 45.1% of theory,
EXAMPLE I 1-benzyl-<strong>[5057-12-5]3,4,7,8-tetrahydro-2,5(1H,6H)-quinolinedione</strong> Prepared analogously to Example H from 3,4,7,8- tetrahydro-2,5(1H,6H)-quinolinedione and benzyl bromide. Melting point: 63.5-65 C., Yield: 98.4% of theory.
EXAMPLE 30 1-(4-Chlorobenzyl)-3,4,7,8-tetrahydro-2,5(1H.6H)-quinolinedione Prepared analogously to Example 29 from 3,4,7,8- tetrahydro-2,5(1H,6H)-quinolinedione and 4-chlorobenzyl- chloride. Melting point: 100-102 C., Yield: 55.4% of theory.
EXAMPLE 29 1-Carbomethoxymethyl-<strong>[5057-12-5]3,4,7,8-tetrahydro-2,5(1H,6H)-quinolinedione</strong> 3.17 g (0.019 mol) of <strong>[5057-12-5]3,4,7,8-tetrahydro-2,5(1H,6H)-quinolinedione</strong> are dissolved in 25 ml of dimethylformamide, mixed with 5.3 g (1.2*0.019 mol) of anhydrous. potassium carbonate and then with 3.52 g (2*0.019 mol) of methyl bromoacetate and the mixture is stirred for 16 hours at ambient temperature. The mixture is neutralised with methanolic hydrochloric acid and evaporated down in a rotary evaporator. The residue is purified by column chromatography (silica gel, eluant: cyclohexane/ethyl acetate (1:1)). Melting point: 87-89 C., Yield: 3.46 g (76% of theory).
bromo-3,4,5,6,7,8-hexahydrocarbostyril-5-one[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
With bromine; In tetrachloromethane;
EXAMPLE 7 Preparation of Compound of Formula II A solution of 3.6 g of bromine in 50 ml of carbon tetrachloride was added, while stirring under ice-cooling, to a solution of 4.0 g of <strong>[5057-12-5]3,4,5,6,7,8-hexahydrocarbostyril-5-one</strong> in 50 ml of carbon tetrachloride. After allowing the mixture to stand for one minute, the precipitate formed was removed by decantation. The carbon tetrachloride layer was distilled at room temperature to remove the solvent (CCl4), and the resulting crystals were combined with the above precipitate followed by being washed with acetone to give quantitatively 8-(or 6-) bromo-<strong>[5057-12-5]3,4,5,6,7,8-hexahydrocarbostyril-5-one</strong> having a melting point of 126-127 C. as yellow crystals.
With ammonium acetate; at 80.0℃; for 5.0h;Inert atmosphere;
General procedure: 1,3-Dicarbonyls (8.9 mmol, 1 equiv.) followed by ammonium acetate (10.6 mmol, 1.2 mmol, 1.2 equiv.) were added to the solution of acrylic acid (10.6 mmol, 1.2 equiv.). The reactant mass was mixed thoroughly with a spatula and heated at 80 C with stirring under a nitrogen atmosphere for 5 h. After cooling, the reaction mixture was diluted with 10mL distilled water and extracted twice with ethyl acetate (210 mL). The organic extracts were dried over anhydrous Na2SO4. After filtration, the solvent was evaporated under reduced pressure and subjected to column chromatography (ethyl acetate=hexane) to obtain pure products. The characterization data of the compounds are given.
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%.
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