54197-66-9

Basic information

• Product Name: 6-Hydroxy-2(1H)-3,4-dihydroquinolinone
• Synonyms: AURORA KA-4814;6-HYDROXY-1,2,3,4-TETRAHYDRO-2-QUINOLINONE;6-HYDROXY-2(1H)-3,4-DIHYDROQUINOLINONE;6-HQ;6-HYDROXYL-3,4-DIHYDROCARBOSTYRIL;6-HYDROXY-3,4-DIHYDRO-1H-QUINOLIN-2-ONE;6-HYDROXY-3,4-DIHYDRO-2(1H)-QUINOLINONE;6-HYDROXY-3,4-DIHYDRO-2-QUINOLINONE
• CAS NO: 54197-66-9
• Molecular Formula: C₉H₉NO₂
• Molecular Weight: 163.17
• EINECS: 1312995-182-4
• Product Categories: Fluorobenzene;Alcohols and Derivatives;Heterocycles;Aromatic Ethers;Quinoline derivatives;API intermediates;(intermediate of cilostazol);Various Metabolites and Impurities;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals
• Mol File: 54197-66-9.mol
• Article Data: 18

Chemical Properties

• Melting Point: 236-240 °C
• Boiling Point: 424.5 °C at 760 mmHg
• Flash Point: 210.5 °C
• Appearance: Off-white solid
• Density: 1.282 g/cm³
• Vapor Pressure: 8.35E-08mmHg at 25°C
• Refractive Index: 1.604
• Storage Temp.: Room temperature.
• PKA: 9.86±0.20(Predicted)
• CAS DataBase Reference: 6-Hydroxy-2(1H)-3,4-dihydroquinolinone(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Hydroxy-2(1H)-3,4-dihydroquinolinone(54197-66-9)
• EPA Substance Registry System: 6-Hydroxy-2(1H)-3,4-dihydroquinolinone(54197-66-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 54197-66-9(Hazardous Substances Data)

Usage

Chemical Properties

Off-white solid

Uses

A metabolite of Cilostazole.

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

Upstream product

• 19314-10-4 3-chloro-propionic acid-(4-hydroxy-anilide) 
• 19314-15-9 3-chloro-propionic acid p-phenetidide 
• 91523-37-4 N-methoxy-3,4-dihydro-1H-quinolin-2-one 
• 553-03-7 3,4-dihydro-2(1H)-quinolone 
• 123-30-8 4-amino-phenol 
• 625-36-5 2-chloropropionyl chloride 
• 7446-70-0 aluminium trichloride 
• 19313-87-2 N-(4-methoxyphenyl)-β-chloropropanamide 
• 77248-69-2 C₉H₇NO₅ 
• 635-46-1 1,2,3,4-tetrahydroisoquinoline 
• 3460-04-6 3-chloro-N-phenylpropionamide 
• 62-53-3 aniline 
• 22246-13-5 6-amino-3,4-dihydro-1H-quinolin-2-one 
• 104-94-9 4-methoxy-aniline 

Downstream Products

• 73963-70-9 6-[3-(1-Phenyltetrazol-5-yl)propoxy]-3,4-dihydrocarbostyril 
• 78876-16-1 6-<3-(1-cyclohexyl-5-tetrazolyl)propoxy>-2-oxo-1,2,3,4-tetrahydroquinoline 
• 73963-71-0 6-[3-(1-Cyclohexylmethyltetrazol-5-yl)propoxy]-3,4-dihydrocarbostyril 
• 86843-26-7 6-[5-(1-Cyclohexyl-1H-tetrazol-5-yl)-pentyloxy]-3,4-dihydro-1H-quinolin-2-one 
• 78876-17-2 6-[4-(1-Cyclohexylmethyl-1H-tetrazol-5-yl)-butoxy]-3,4-dihydro-1H-quinolin-2-one 
• 86843-27-8 6-{4-[1-(2-Cyclohexyl-ethyl)-1H-tetrazol-5-yl]-butoxy}-3,4-dihydro-1H-quinolin-2-one 
• 73963-69-6 6-[3-(1-Benzyltetrazol-5-yl)propoxy]-3,4-dihydrocarbostyril 
• 73963-72-1 6-[4-(1-cyclohexyl-1H-tetrazol-5-yl)butoxy]-3,4-dihydrocarbostyril 
• 87153-00-2 6-{4-[1-((1R,3S)-3-Benzyloxy-cyclohexyl)-1H-tetrazol-5-yl]-butoxy}-3,4-dihydro-1H-quinolin-2-one 
• 87153-00-2 6-{4-[1-((1R,3R)-3-Benzyloxy-cyclohexyl)-1H-tetrazol-5-yl]-butoxy}-3,4-dihydro-1H-quinolin-2-one 
• 87152-97-4 6-(4-<1-(trans-4-benzyloxycyclohexyl)-1H-5-tetrazolyl>butoxy)-2-oxo-1,2,3,4-tetrahydroquinoline 
• 87152-98-5 6-{4-[1-((1R,2S)-2-Benzyloxy-cyclohexyl)-1H-tetrazol-5-yl]-butoxy}-3,4-dihydro-1H-quinolin-2-one 
• 87152-98-5 6-{4-[1-((1R,2R)-2-Benzyloxy-cyclohexyl)-1H-tetrazol-5-yl]-butoxy}-3,4-dihydro-1H-quinolin-2-one 
• 54197-64-7 6-methoxy-2-oxo-1,2,3,4-tetrahydroquinoline 

Relevant articles and documents

Preparation method 6 -hydroxy -3-4 - dihydro -2 (1H)-quinolone (by machine translation)

HCl is added to the reaction solvent N, N - dimethylacetamide, HCl is added, solid matter is precipitated, filtered 2, the filter cake is washed 6 - times with ethanol, and then the 6 - residual solvent residue is 1 - 3 hours removed by -3 drying to 4 - obtain -2 the final product -3 hydroxyl 4 - 3 -2 dihydro 4 - 3 - (1H)-quinolonecarboxylic acid, N, N-(4 - 20 - 30 °C methoxyphenyl 0.05 - 0.2) propionamide. 1 is added 1H to the reaction solvent N, N-dimethylacetamide, and then the solvent is evaporated. The ionic liquid catalyst is high in thermal stability and catalytic performance, high in product yield, simple in reaction steps, easy to control and suitable for industrial production characteristics. (by machine translation)

Preparation method of 6-hydroxy-3,4-dihydro-2(1H)quinolinone

The invention belongs to the field of preparation of intermediates in chemical engineering, and particularly relates to a preparation method of 6-hydroxy-3,4-dihydro-2(1H)quinolinone. The preparationmethod comprises the following steps of using aniline and 3-chloropropionyl chloride as raw materials; performing cyclization, nitrification, reduction and diazotization hydrolysis, so as to synthesize the target product, namely 6-hydroxy-3,4-dihydro-2(1H)quinolinone. The preparation method has the advantages that the reaction conditions are mild, the cost is reduced, and the yield rate is increased.

Preparation method of cilostazol

The invention discloses a preparation method of cilostazol and belongs to the field of medicines. The preparation method comprises the following steps: firstly, reacting 4-methoxyaniline with 3-chloropropionyl chloride in the presence of a solvent or no solvent; after a TLC (thin layer chromatography) detecting reaction is finished, adding aluminum trichloride into a system, and carrying out temperature raising reaction for 1 to 16 hours to obtain 6-hydroxy-3,4-dihydroquinoline-2-keto; secondly, in the presence of alkali, carrying out heating reaction on the 6-hydroxy-3,4-dihydroquinoline-2-keto obtained in the first step and 5-(4-chlorobutyl)-1-cyclohexanyl tetrazole in normal propyl alcohol to obtain the cilostazol. The high-purity cilostazol can be obtained by adopting the method disclosed by the invention; the preparation method has the advantages of few steps of the whole synthetic route, high yield, low cost, less wastewater and suitability for industrial production.