553-03-7

Basic information

• Product Name: 1,2,3,4-Tetrahydroquinolin-2-one
• Synonyms: HYDROCARBOSTYRIL;DIHYDROCARBOSTYRIL;3,4-DIHYDRO-2(H)-QUINOLINE;3,4-DIHYDRO-2(1H)-QUINOLINONE;3,4-DIHYDRO-2(1H)-QUINOLONE;3,4-DIHYDRO-1H-QUINOLIN-2-ONE;1,2,3,4-Tetrahydroquinolin-2-one;2-OXO-1,2,3,4-TETRAHYDROQUINOLINE
• CAS NO: 553-03-7
• Molecular Formula: C₉H₉NO
• Molecular Weight: 147.17
• EINECS: 1592732-453-0
• Product Categories: Heterocycles;pharmacetical;API intermediates;Quinolines, Isoquinolines & Quinoxalines
• Mol File: 553-03-7.mol
• Article Data: 34

Chemical Properties

• Melting Point: 165-167 °C(lit.)
• Boiling Point: 267.28°C (rough estimate)
• Flash Point: 189.4 °C
• Appearance: Off-white/Crystalline Powder
• Density: 1.1135 (rough estimate)
• Vapor Pressure: 0.000194mmHg at 25°C
• Refractive Index: 1.5200 (estimate)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: 14.76±0.20(Predicted)
• Water Solubility: Slightly soluble in water.
• Sensitive: Light Sensitive
• Merck: 13,4800
• CAS DataBase Reference: 1,2,3,4-Tetrahydroquinolin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,3,4-Tetrahydroquinolin-2-one(553-03-7)
• EPA Substance Registry System: 1,2,3,4-Tetrahydroquinolin-2-one(553-03-7)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38-43
• Safety Statements: 26-36/37
• RIDADR: 2811
• WGK Germany: 2
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 553-03-7(Hazardous Substances Data)

Usage

Chemical Properties

Off-white crystalline powder

Uses

Different sources of media describe the Uses of 553-03-7 differently. You can refer to the following data:
1. 3,4-Dihydro-2-(1H)-quinolinone may be employed as medium supplement in the culture medium of Pseudomonas ayucida during enrichment culture experiments. It is used to prepare potent bicyclic peptide deformylase inhibitors with antibacterial effects. It is also used to synthesize substituted iminopiperidines as inhibitors of human nitric oxide synthase isoforms.
2. 3,4-Dihydro-2(1H)-quinolinone may be employed as medium supplement in the culture medium of Pseudomonas ayucida during enrichment culture experiments.

Synthesis Reference(s)

Journal of the American Chemical Society, 89, p. 7131, 1967 DOI: 10.1021/ja01002a061Tetrahedron Letters, 36, p. 125, 1995 DOI: 10.1016/0040-4039(94)02191-D

General Description

Series of 3,4-dihydro-2(1H)-quinolinone derivatives having sigma-1 receptor (σ1R) antagonist activity have been synthesized. 3,4-dihydro-2((1)H)-quinolinones have been synthesized using N-(1′-alkoxy)cyclopropyl-2-haloanilines as starting reagent. Cyclopropane ring expansion in the presence of palladium catalyst is the major step involved in the synthesis. Library of 3,4-dihydro-2(1H)-quinolinones have been synthesized through the rearrangement of β-lactam intermediates on the solid-phase

InChI:InChI=1/C9H9NO/c11-9-6-5-7-3-1-2-4-8(7)10-9/h1-4H,5-6H2,(H,10,11)

Upstream product

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• 1154703-35-1 3-(2-t-butoxycarbonylaminophenyl)propionic acid 2-(11,17-dihydroxy-10,13-dimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-2-oxo-ethyl ester 
• 83-33-0 inden-1-one 
• 1154703-42-0 C₃₀H₃₉NO₆ 
• 850413-97-7 (2-{2-[9-((2R,4S,5R)-4-Hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-6-oxo-6,9-dihydro-1H-purin-2-ylcarbamoyl]-ethyl}-phenyl)-carbamic acid 2-trimethylsilanyl-ethyl ester 
• 850413-95-5 (2-{2-[9-((2R,4S,5R)-4-Hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-9H-purin-6-ylcarbamoyl]-ethyl}-phenyl)-carbamic acid 2-trimethylsilanyl-ethyl ester 
• 850413-94-4 (2-{2-[1-((2R,4S,5R)-4-Hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-2-oxo-1,2-dihydro-pyrimidin-4-ylcarbamoyl]-ethyl}-phenyl)-carbamic acid 2-trimethylsilanyl-ethyl ester 
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• 7647-01-0 hydrogenchloride 
• 64-19-7 acetic acid 

Downstream Products

• 240798-90-7 N-benzyloxymethyl-3,4-dihydro-2(H)-quinolinone 
• 67176-93-6 1-phenyl-1,2,3,4-tetrahydroquinolin-2-one 
• 92367-59-4 3,3-dimethyl-3,4-dihydroquinolin-2(1H)-one 
• 1247021-75-5 1-[2-(trifluoromethyl)benzyl]-3,4-dihydroquinolin-2(1H)-one 
• 1243651-55-9 3,4-dihydro-1-[3-(4-(2,3-dichlorophenyl)piperazin-1-yl)propyl]quinolin-2(1H)-one 
• 1243651-30-0 3,4-dihydro-1-[3-(4-(4-methoxyphenyl)piperazin-1-yl)propyl]quinolin-2(1H)-one 
• 1620-30-0 diphenyl(pyridin-4-yl)methanol 
• 613-18-3 2,3-dichloroquinoline 
• 17194-19-3 3-[2-(3,4-Dichloro-benzoylamino)-phenyl]-propionic acid 
• 66657-42-9 2-oxo-1,2,3,4-tetrahydroquinoline-6-sulfonyl chloride 
• 31883-79-1 3-methyl-3,4-dihydroquinolin-2(1H)-one 
• 115706-37-1 2-(1,2,3,4-tetrahydro-2-oxoquinolin-1-yl)propionic acid 
• 61122-82-5 6-chloroacetyl-1,2,3,4-tetrahydroquinolin-2-one 
• 62245-12-9 6-acetyl-3,4-dihydro-2(1H)-quinolinone 

Relevant articles and documents

Dehydrogenative and Redox-Neutral N-Heterocyclization of Aminoalcohols Catalyzed by Manganese Pincer Complexes

A new manganese catalyzed heterocyclization of aminoalcohols has been accomplished. A wide range of heterocycles were synthesized, including 1,2,3,4-tetrahydroquinolines, dihydroquinolinones, and 2,3,4,5-tetrahydro-1H-benzo[b]azepines. The reaction is performed under mild reaction conditions using air and moisture stable manganese catalysts. The desired heterocycles were obtained in good to excellent yields.

Formal Deoxygenative Hydrogenation of Lactams Using PNHP-Pincer Ruthenium Complexes under Nonacidic Conditions

A formal deoxygenative hydrogenation of amides to amines with RuCl2(NHC)(PNHP) (NHC = 1,3-dimethylimizadol-2-ylidene, PNHP = bis(2-diphenylphosphinoethyl)amine) is described. Various secondary amides, especially NH-lactams, are reduced with H2 (3.0-5.0 MPa) to amines at a temperature range of 120-150 °C with 1.0-2.0 mol % of PNHP-Ru catalysts in the presence of Cs2CO3. This process consists of (1) deaminative hydrogenation of secondary amides to generate primary amines and alcohols, (2) dehydrogenative coupling of the transient amines with alcohols to generate imines, and (3) hydrogenation of imines to give the formally deoxygenated secondary amine products.

Enabling CO Insertion into o-Nitrostyrenes beyond Reduction for Selective Access to Indolin-2-one and Dihydroquinolin-2-one Derivatives

The transition metal-catalyzed reductive cyclization of o-nitrostyrene in the presence of carbon monoxide (CO) has been developed to be a general synthetic route to an indole skeleton, wherein CO was used as a reductant to deoxidize nitroarene into nitrosoarene and/or nitrene with CO2 release, but the selective insertion of CO into the heterocyclic product with higher atom economy has not yet been realized. Herein, the Pd-catalyzed reduction of o-nitrostyrene by CO and its regioselective insertion were efficiently achieved to produce synthetically useful five- and six-membered benzo-fused lactams. Detailed investigations revealed that the chemoselectivity to indole or lactam was sensitive to the nature of the counteranions of Pd2+ precursors, whereas ligands significantly decided the carbonylative regioselectivity by different reaction pathways. Using PdCl2/PPh3/B(OH)3 (condition A), an olefin hydrocarboxylation was primarily initiated followed by partial reduction of the NO2 moiety and cyclization reaction to give N-hydroxyl indolin-2-one, which was further catalytically reduced by CO to afford the indolin-2-one as the final product with up to 95% yield. When the reaction was conducted under the Pd(TFA)2/BINAP/TsOH·H2O system (condition B), complete deoxygenation and carbonylation of the NO2 group occurred initially to yield the corresponding isocyanate followed by internal hydrocyclization to generate 3,4-dihydroquinolin-2-one with up to 98% yield. Importantly, the methodology could be efficiently applied in the synthesis of marketed drug Aripiprazole.