7,8-Dihydroquinolin-6(5H)-one

Base Information

• Chemical Name: 7,8-Dihydroquinolin-6(5H)-one
• CAS No.: 27463-91-8
• Molecular Formula: C₉H₉NO
• Molecular Weight: 147.177
• Hs Code.: 2933499090
• European Community (EC) Number: 832-792-6
• DSSTox Substance ID: DTXSID20507021
• Wikidata: Q72466197
• Mol file: 27463-91-8.mol

Synonyms:27463-91-8;7,8-DIHYDROQUINOLIN-6(5H)-ONE;7,8-DIHYDRO-6(5H)-QUINOLINONE;7,8-dihydro-5H-quinolin-6-one;5,6,7,8-tetrahydroquinolin-6-one;6(5H)-Quinolinone,7,8-dihydro-;6(5H)-Quinolinone, 7,8-dihydro-;SCHEMBL10665026;DTXSID20507021;7, 8-dihydro-5H-quinolin-6-one;AMY13875;MFCD06659761;AKOS026727299;AB26260;AT37836;BS-13510;CS-0102419;FT-0758160;EN300-49955

Chemical Property of 7,8-Dihydroquinolin-6(5H)-one

Chemical Property:

• Vapor Pressure: 0.002mmHg at 25°C
• Refractive Index: 1.569
• Boiling Point: 287.894 °C at 760 mmHg
• Flash Point: 135.558 °C
• PSA: 29.96000
• Density: 1.168 g/cm³
• LogP: 1.13940
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 147.068413911
• Heavy Atom Count: 11
• Complexity: 167

Purity/Quality:

98% ^*data from raw suppliers

7,8-Dihydroquinolin-6(5H)-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC2=C(CC1=O)C=CC=N2

Technology Process of 7,8-Dihydroquinolin-6(5H)-one

There total 15 articles about 7,8-Dihydroquinolin-6(5H)-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: 85.0%

7′,8′-dihydro-5′H-spiro[[1,3]dioxolane-2,6′-quinoline] → 7,8-dihydroquinolin-6(5H)-one (27463-91-8)

Guidance literature:

With phosphoric acid; In water; at 80 ℃; for 8h;

DOI:10.1021/acs.joc.0c03038

Reference yield: 72.0%

5-(Phenylsulfonyl)-6-oxo-5,6,7,8-tetrahydroquinoline (76915-84-9) → 7,8-dihydroquinolin-6(5H)-one (27463-91-8)

Guidance literature:

With nickel; In ethanol; acetone; for 1h; Heating;

DOI:10.1021/jo00323a016

Reference yield:

2,3-Lutidine (583-61-9) → 7,8-dihydroquinolin-6(5H)-one (27463-91-8)

Guidance literature:

Multi-step reaction with 9 steps

1: azobis(isobutyronitrile), NBS / CCl₄ / 1.5 h / Heating; Irradiation

2: 58 percent / ethanol / 1 h / Heating

3: aq. NaIO₄ / methanol / 6 h / Ambient temperature

4: KMnO₄ / methanol; H₂O / 0.5 h / Ambient temperature

5: 84 percent / NBS, azobis(isobutyronitrile) / CCl₄ / 2 h / Heating; Irradiation

6: 1.) LDA, HMPT, 2.) / 1.) THF, 0 deg C, 1 h, 2.) -78 deg C, 0.5 h

7: Raney nickel / ethanol; acetone / 1 h / 60 °C

8: 81 percent / sodium hydride / tetrahydrofuran; dimethylsulfoxide / 1 h / Ambient temperature

9: 72 percent / Raney nickel / acetone; ethanol / 1 h / Heating

With N,N,N,N,N,N-hexamethylphosphoric triamide; potassium permanganate; sodium periodate; N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); nickel; sodium hydride; lithium diisopropyl amide; In tetrahydrofuran; methanol; tetrachloromethane; ethanol; water; dimethyl sulfoxide; acetone;

DOI:10.1021/jo00323a016

upstream raw materials:

5-(Phenylsulfonyl)-6-oxo-5,6,7,8-tetrahydroquinoline

2,3-Lutidine

(2-methylpyridin-3-yl)methanol

ethyl 2-methyl nicotinate

Refernces

• 1、 Zhu, Zixi,Glinkerman, Christopher M.,Boger, Dale L.. "Selective N1/N4 1,4-Cycloaddition of 1,2,4,5-Tetrazines Enabled by Solvent Hydrogen Bonding". . p. 20778 - 20787. Retrieved 2020/12/22.