1,2,3,4-Tetrahydroquinolin-2-one

Base Information

• Chemical Name: 1,2,3,4-Tetrahydroquinolin-2-one
• CAS No.: 553-03-7
• Molecular Formula: C9H9NO
• Molecular Weight: 147.177
• Hs Code.: 29337900
• Mol file: 553-03-7.mol

Synonyms:Carbostyril,3,4-dihydro- (7CI,8CI);Hydrocarbostyril (6CI);1,2,3,4-Tetrahydro-2(1H)-quinolinone;1,2,3,4-Tetrahydro-2-oxoquinoline;1,2,3,4-Tetrahydroquinolin-2-one;2-Oxo-1,2,3,4-tetrahydroquinoline;3,4-Dihydro-1H-quinolin-2-one;3,4-Dihydro-2(1H)-quinolone;3,4-Dihydro-2-quinolinol;3,4-Dihydro-2-quinolinone;3,4-Dihydro-2-quinolone;3,4-Dihydrocarbostyril;3,4-Dihydroquinolin-2(1H)-one;NSC 49170;o-Aminohydrocinnamic acid lactam;3,4-Dihydro-2(1H)-quinolinone;

Chemical Property of 1,2,3,4-Tetrahydroquinolin-2-one

Chemical Property:

• Appearance/Colour: Off-white crystalline powder
• Vapor Pressure: 0.000194mmHg at 25°C
• Melting Point: 165-167 °C
• Refractive Index: 1.564
• Boiling Point: 328.1 °C at 760 mmHg
• PKA: 14.76±0.20(Predicted)
• Flash Point: 189.4 °C
• PSA: 29.10000
• Density: 1.142 g/cm³
• LogP: 1.70930
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Sensitive.: Light Sensitive
• Water Solubility.: Slightly soluble in water.

Purity/Quality:

99% ^*data from raw suppliers

3,4-Dihydro-2-quinolone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38-43
• Safety Statements: 26-36/37

MSDS Files:

SDS file from LookChem

Useful:

• General Description: 1,2,3,4-Tetrahydroquinolin-2-one, also known as dihydroquinolinone, is a six-membered nitrogen heterocycle with notable pharmaceutical relevance due to its biological activities. It can be synthesized via intramolecular aza-Michael cyclization of 2’-aminochalcones, with mesoporous aluminosilicates like MCM-41 proving effective as catalysts for high-yield production. The compound's structural framework makes it valuable in medicinal chemistry, though challenges such as catalyst deactivation must be addressed during synthesis.

Technology Process of 1,2,3,4-Tetrahydroquinolin-2-one

There total 47 articles about 1,2,3,4-Tetrahydroquinolin-2-one which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 73.0%

6-bromo-3,4-dihydro-1H-quinolin-2-one (3279-90-1) → 1,2,3,4-tetrahydroisoquinoline (635-46-1) + 3,4-dihydro-2(1H)-quinolone (553-03-7) + 6-bromo-1,2,3,4-tetrahydroquinoline (22190-35-8)

Guidance literature:

With [RuCl₂(N-heterocyclic carbene)(bis[2-(diphenylphosphino)ethyl]amine)]; hydrogen; caesium carbonate; In toluene; butan-1-ol; at 120 ℃; for 6h; under 22502.3 Torr; Schlenk technique; Autoclave;

DOI:10.1021/acs.orglett.9b03878

Reference yield: 71.0%

2-quinolone (59-31-4,70254-42-1,493-62-9) → 1,2,3,4-tetrahydroisoquinoline (635-46-1) + 3,4-dihydro-2(1H)-quinolone (553-03-7)

Guidance literature:

With hydrogenchloride; samarium; for 0.166667h; Ambient temperature;

DOI:10.1248/cpb.43.1422

Reference yield: 68.0%

1,2,3,4-tetrahydroisoquinoline (635-46-1) → quinoline (91-22-5) + 3,4-dihydro-2(1H)-quinolone (553-03-7)

Guidance literature:

With glucose dehydrogenase; D-glucose; cytochrome P₄₅₀ enzyme CYP₁₀₂A₁ A₈₂M/F₈₇A/H₁₇₁L/E₂₆₇F/Q₃₀₇H/N₃₁₉Y mutant; C₂₁H₂₅N₇O₁₇P₃^(3-)*2H⁽¹⁺⁾*Na⁽¹⁺⁾; In aq. phosphate buffer; ethanol; at 20 ℃; for 4h; pH=8.4; Catalytic behavior; Enzymatic reaction;

DOI:10.1002/anie.201904157

upstream raw materials:

(2-nitro-benzyl)-malonic acid

1-phenylmethyl-4-piperidone

dihydrocinnamamide

N-hydroxy-3-phenylpropanamide

Downstream raw materials:

1,2,3,4-tetrahydroisoquinoline

2,3-dichloroquinoline

3,4-dihydro-(1H)-quinoline-2-thione

6-bromo-3,4-dihydro-1H-quinolin-2-one

Refernces

Use of Mesoporous Molecular Sieves in the Production of Fine Chemicals: Preparation of Dihydroquinolinones of Pharmaceutical Interest from 2′-Aminochalcones

10.1002/cctc.201501403

The study investigates the use of mesoporous molecular sieves, particularly MCM-41, in the production of fine chemicals, focusing on the synthesis of dihydroquinolinones of pharmaceutical interest from 2’-aminochalcones. Dihydroquinolinones are six-membered nitrogen heterocyclic compounds with significant biological activities, making them valuable for pharmaceutical applications. The synthesis typically involves the base or acid-catalyzed intramolecular aza-Michael cyclization of 2’-aminochalcones. The study explores various catalysts, including zeolites and mesoporous materials, to optimize the yield and catalyst life. It highlights the challenges of catalyst deactivation due to strong adsorption of reactants and products, and demonstrates that mesoporous aluminosilicates like MCM-41 with a Si/Al ratio of 15 offer high activity and selectivity, achieving excellent yields of dihydroquinolinones. Additionally, the study presents a one-pot synthesis process starting from 2’-nitrochalcones using a bifunctional metal–acid catalyst, achieving high yields and selectivity in a short reaction time.