6-Hydroxy-2(1H)-3,4-dihydroquinolinone Chemical Properties

Melting point:

236-240 °C

Boiling point:

424.5±45.0 °C(Predicted)

Density 

1.282±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

DMSO (Slightly), Methanol (Slightly, Heated)

form 

solid

pka

9.86±0.20(Predicted)

color 

White to Almost white

InChI

InChI=1S/C9H9NO2/c11-7-2-3-8-6(5-7)1-4-9(12)10-8/h2-3,5,11H,1,4H2,(H,10,12)

InChIKey

HOSGXJWQVBHGLT-UHFFFAOYSA-N

SMILES

N1C2=C(C=C(O)C=C2)CCC1=O

CAS DataBase Reference

54197-66-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26

WGK Germany 

3

Hazard Note 

Irritant

HS Code 

2933790002

6-Hydroxy-2(1H)-3,4-dihydroquinolinone Usage And Synthesis

Chemical Properties

6-Hydroxy-2(1H)-3,4-dihydroquinolinone Appearance is white to almost white powder to crystal, Melting point 238°C, Store at -20° C.

Uses

A metabolite of Cilostazole.

Synthesis

2) 98 g of 3-chloro-N-(4-methoxyphenyl)acrylamide obtained from step 1) was mixed with N-(4-methoxyphenyl)-3-chloroacrylamide, 500 mL of tetrahydrofuran and 98 g of palladium chloride. The reaction mixture was heated to 100 °C under 5 MPa pressure and maintained at that temperature. Upon completion of the reaction, it was cooled to room temperature and then maintained at 110°C for 3 hours. Subsequently, filtration was performed and the filtrate was rotary evaporated to dryness to obtain 6-hydroxy-3,4-dihydro-2(1H)-quinolone crude.3) The 6-hydroxy-3,4-dihydro-2(1H)-quinolone crude obtained in step 2) was dissolved in 50 mL of ethanol, recrystallized and decolorized using activated carbon. After filtration, 74 g of 6-hydroxy-3,4-dihydro-2(1H)-quinolinone was obtained as an off-white solid in 95% yield. The total yield was 85%.

References

[1] Patent: CN108383781, 2018, A. Location in patent: Paragraph 0033; 0034
[2] Patent: CN107325078, 2017, A. Location in patent: Paragraph 0039-0040; 0043-0044; 0046-0047; 0049-0050; 0052
[3] Journal of the Chinese Chemical Society, 2000, vol. 47, # 1, p. 155 - 162
[4] Heterocycles, 2009, vol. 78, # 1, p. 189 - 195
[5] Asian Journal of Chemistry, 2011, vol. 23, # 4, p. 1655 - 1660

6-Hydroxy-2(1H)-3,4-dihydroquinolinone(54197-66-9)Related Product Information

• 1,3-Dihydroxyacetone
• Triclosan
• Dihydromyrcenol
• 1-Hydroxyethylidene-1,1-diphosphonic acid
• Butylated Hydroxytoluene
• CHLOROPHOSPHONAZO III
• 2-Quinolinol
• 6-HYDROXY-3,4-DIHYDRO-1H-QUINOLIN-2-ONE,6-HYDROXY-2-OXO-1,2,3,4-TETRAHYDROQUINOLINE
• 6-Hydroxy-1-tetralone
• 5-AZIDO-VALERIANIC ACID
• 3-azidopropanoic acid
• Cilostazol
• 6-Methoxy-3,4-dihydro-1H-quinolin-2-one
• Cilostazol Related Compound C (50 mg) (1-(4-(5-Cyclohexyl-1H-tetrazol-1-yl)butyl)-6-(4-(1-cyclohexyl-1H-tetrazol-5-yl)butoxy)-3,4-dihydroquinolin-2(1H)-one)
• Cilostazol Impurity
• GJXNGCFWGJQETE-UHFFFAOYSA-N
• 4-CIS-HYDROXY CILOSTAZOL
• 6-[3-(1-CYCLOHEXYL-1H-TETRAZOL-5-YL) PROPOXY]-2(1H)-QUINOLINONE