7-Hydroxyquinolinone Chemical Properties

Melting point:

187-192°C

Boiling point:

426.8±45.0 °C(Predicted)

Density 

1.337±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

DMSO (Slightly), Methanol (Slightly, Sonicated)

form 

Solid

pka

9.32±0.20(Predicted)

color 

Off-White to Pale Yellow

Water Solubility 

Water: Insoluble

InChI

InChI=1S/C9H7NO2/c11-7-3-1-6-2-4-9(12)10-8(6)5-7/h1-5,11H,(H,10,12)

InChIKey

DBSPUDKBNOZFMX-UHFFFAOYSA-N

SMILES

N1C2=C(C=CC(O)=C2)C=CC1=O

CAS DataBase Reference

70500-72-0(CAS DataBase Reference)

Safety Information

HS Code 

29334900

7-Hydroxyquinolinone Usage And Synthesis

Chemical Properties

Off-White Solid

Uses

7-Hydroxyquinolone is a substituted carbostyril derivative used as a pharmaceutical intermediate. It is an impurity of aripiprazole quinolinone.

Definition

ChEBI: 7-hydroxyquinolin-2(1H)-one is a monohydroxyquinoline and a quinolone.

Synthesis

General procedure for the synthesis of 7-hydroxyquinolin-2(1H)-one from N-(3-methoxyphenyl)cinnamamide: Aluminum trichloride (3.16 g, 23.69 mmol) was added batchwise to a suspension of chlorobenzene (30 mL) of compound 3 (1 g, 3.95 mmol) in an ice bath. The reaction mixture was gradually warmed up to 120 °C and kept at reflux for 3 hours. The reaction process was monitored by thin layer chromatography (TLC). After completion of the reaction, the reaction mixture was concentrated to dryness under reduced pressure and the residue was purified by silica gel column chromatography to afford compound 4 in 54% yield.

References

[1] Synthesis, 1997, # 1, p. 87 - 90
[2] Tetrahedron Letters, 1999, vol. 40, # 24, p. 4505 - 4506
[3] Journal of Medicinal Chemistry, 2015, vol. 58, # 14, p. 5561 - 5578
[4] Patent: CN108101926, 2018, A. Location in patent: Paragraph 0033; 0034; 0035
[5] Patent: WO2008/24481, 2008, A2. Location in patent: Page/Page column 32

7-Hydroxyquinolinone(70500-72-0)Related Product Information

• 4'-Hydroxyacetophenone
• CHLOROPHOSPHONAZO III
• 2-Quinolinol
• Quinclorac
• Quinhydrone
• Ethoxyquin
• Isoquinoline
• 8-Hydroxyquinoline
• Brexpiprazole
• 8-(2,3-Dichlorophenyl)-8-aza-5-azoniaspiro[4.5]decane BroMide
• 5-Hydroxy-3,4-dihydroquinolin-2(1H)-one
• 3,4-Dihydro-7-hydroxy-2(1H)-quinolinone
• 7-(4-BROMOBUTOXY)-QUINOLINE-2(1H)-ONE
• Brexpiprazole Impurity 20
• Thianaphthene
• Brexpiprazole Impurity
• Brexpiprazole Impurity 2
• Brexpiprazole sulfoxide impurity