7-Hydroxy-2(1H)-quinolinone
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7-Hydroxy-2(1H)-quinolinone
structure -
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CAS No:
70500-72-0
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Formula:
C9H7NO2
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Chemical Name:
7-Hydroxy-2(1H)-quinolinone
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Synonyms:
2(1H)-Quinolinone,7-hydroxy-;7-Hydroxy-2(1H)-quinolinone;7-Hydroxycarbostyril;7-Hydroxy-1H-quinolin-2-one;2,7-Dihydroxyquinoline
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CAS No:
7-Hydroxy-2(1H)-quinolinone Basic Attributes
161.16
161.16
1308068-626-2
3B25C3NP9L
DTXSID30450372
2933499090
Characteristics
49.3
0.9
Pale yellow powder
1.4±0.1 g/cm3
308-315 °C (decomp) @ Solvent: Water
403.7ºC at 760 mmHg
220.9±23.2 °C
1.743
Refrigerator
4.28E-07mmHg at 25°C
Safety Information
22-43
S36/37
Xn, Xi
P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, P501
H302
|Warning|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 3 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
7-Hydroxy-2(1H)-quinolinone Use and Manufacturing
To a suspension of compound 3 (1 g, 3.95 mmol) in chlorobenzene (30 mL) was added portionwise aluminum trichloride (3.16 g, 23.69 mmoL) under ice bath.The reaction system was gradually heated to 120 ° C, refluxed for 3-5 h, and the reaction system was monitored by TLC.After the completion of the reaction, the reaction system was evaporated to dryness under reduced pressure and purified by silica gel column chromatography.Compound 4 was obtained in 54percent yield.Suggest an editIntermediate 14:[0130] AICI[00220] N-(3-methoxyphenyl)cinnamamide (18 g, 71 mmol ) was added AICIInto a 1000mL reaction flask put 100g of 3, 4-dihydro-7-hydroxyl-2-quinolinone, and add 500mL of tetrahydrofuran, and then add 140g of DDQ, after that heated at 66 ° C, stirred and refluxed for 4 hours, after the reaction is complete, add 1mol / L sodium thiosulfate 500mL aqueous solution, and then filtered and dried, and then obtained 7-hydroxyl-2-quinolinone as an off-white powder 88g, yield 89percent, purity 99.7percent.To a solution of compound 4 (25 g, 0.153 mol, 1.0 eq) in THF (125 mL) at room temperature under a nitrogen atmosphere and stirred for 10-15 min, 2, 3-dichloro-5, 6-dicyano-1, 4-benzoquinone (DDQ) added portion wise (37.16 g, 0.163, 1.07 eq) to the reaction mixture. Stirred the reaction at 45-50 °C for 2 h. The progress of the reaction monitored by TLC, reaction mixture was cooled to 25-30 °C, added NaHCOA solution of 4, 5-dichloro-3, 6-dihydroxyphthalonitrile (40.86 gm) in tetrahydrofuran (100 ml) was added to a pre-cooled mixture of 7-hydroxy-3, 4-dihydroquinolin-2(1H)-one (25 gm) and tetrahydrofuran (50 ml) at 0-5°C and stirred the reaction mixture for 20 min at the same temperature. Raised the temperature of the reaction mixture to 25-30°C and stirred for 1 1 hrs at the same temperature. Filtered the solid, washed with tetrahydrofuran and suck dried the material. Methanol (125 ml) was added to the obtained compound at 25-30°C. Heated the reaction mixture to 50-55°C and stirred for 1 hr at the same temperature. Cooled the reaction mixture to 25-30°C and stirred for 1 hr at the same temperature. Filtered the solid, washed with methanol and dried the material to get the title compound. (0289) Yield: 20.3 gm.
A substituted carbostyril derivative as pharmaceutical intermediate.
Computed Properties
Molecular Weight:161.16
XLogP3:0.9
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:2
Exact Mass:161.047678466
Monoisotopic Mass:161.047678466
Topological Polar Surface Area:49.3
Heavy Atom Count:12
Complexity:225
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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