5H-Quinindoline

Base Information

• Chemical Name: 5H-Quinindoline
• CAS No.: 243-38-9
• Molecular Formula: C15H10N2
• Molecular Weight: 218.258
• Hs Code.: 2933990090
• European Community (EC) Number: 205-954-3
• NSC Number: 687969
• UNII: QG62RG4773
• DSSTox Substance ID: DTXSID00179028
• Nikkaji Number: J193.688C
• Wikidata: Q6094999
• ChEMBL ID: CHEMBL119830
• Mol file: 243-38-9.mol

Synonyms:6H-indolo(2,3-b)quinoline

Chemical Property of 5H-Quinindoline

Chemical Property:

• Vapor Pressure: 1.71E-08mmHg at 25°C
• Refractive Index: 1.839
• Boiling Point: 468.2 °C at 760 mmHg
• Flash Point: 217.5 °C
• PSA: 28.68000
• Density: 1.336 g/cm³
• LogP: 3.86930
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 218.084398327
• Heavy Atom Count: 17
• Complexity: 291

Purity/Quality:

99% ^*data from raw suppliers

6H-Indolo[2,3-b]quinoline 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C=C3C4=CC=CC=C4NC3=N2

Technology Process of 5H-Quinindoline

There total 125 articles about 5H-Quinindoline 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: 98.0%

11-(2-benzenesulfonylethyl)-11H-10,11-diaza-benzo[b]fluorene (1130682-58-4) → 6H-quinindoline (243-38-9)

Guidance literature:

With potassium tert-butylate; In tetrahydrofuran; at -40 ℃; for 4h;

DOI:10.1039/b816608k

Reference yield: 94.0%

C15H12N2O → 6H-quinindoline (243-38-9)

Guidance literature:

C₁₅H₁₂N₂O; With trichlorophosphate; In acetonitrile; at 0 - 90 ℃; Sealed tube;

With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 120 ℃; Sealed tube;

DOI:10.1039/c7ra05349e

Reference yield: 92.0%

6-(pyridin-2-yl)-6H-indolo[2,3-b]quinoline → 6H-quinindoline (243-38-9)

Guidance literature:

6-(pyridin-2-yl)-6H-indolo[2,3-b]quinoline; With methyl trifluoromethanesulfonate; In dichloromethane; at 0 - 20 ℃; for 12h; Inert atmosphere; Schlenk technique;

With sodium hydroxide; In methanol; dichloromethane; water; at 60 ℃; for 10h; Inert atmosphere; Schlenk technique;

DOI:10.1021/acs.orglett.6b01234

upstream raw materials:

2-oxoindole

(E)-N-(2-aminobenzylidene)-4-methylaniline

1-(quinoline-2-yl)-1H-benzo[d][1,2,3]triazole

2,4-dichloro-3-(2-nitro-phenyl)-quinoline

Downstream raw materials:

neocryptolepine

Refernces

• 1、 Khorshidi, Alireza,Tabatabaeian, Khalil. "Ruthenium-exchanged FAU-Y zeolite catalyzed improvement in the synthesis of 6H-indolo[2,3-b]quinolines". . p. 128 - 131. Retrieved 2011.
• 2、 Kadam, Hari K.,Tilve, Santosh G.. "An Alternate Synthesis of 6H-Indolo[2,3-b]quinoline via One-Pot Alkylation–Dehydration–Cyclization–Aromatization Approach". . p. 2066 - 2069. Retrieved 2016.
• 3、 Yu, Songjie,Li, Yunyun,Zhou, Xukai,Wang, He,Kong, Lingheng,Li, Xingwei. "Access to Structurally Diverse Quinoline-Fused Heterocycles via Rhodium(III)-Catalyzed C-C/C-N Coupling of Bifunctional Substrates". . p. 2812 - 2815. Retrieved 2016.
• 4、 Alajarin,Molina,Vidal. "Formal total synthesis of the alkaloid cryptotackieine (neocryptolepine)". . p. 747 - 748. Retrieved 1997.
• 5、 Aksenov, Alexander V.,Aksenov, Dmitrii A.,Aksenov, Nicolai A.,Arutyunov, Nikolai A.,Gasanova, Amina Z.,Lower, Carolyn,Rubin, Michael. "Synthetic studies towards benzofuro[2,3-b]quinoline and 6H-indolo[2,3-b]quinoline cores: Total synthesis of norneocryptolepine and neocryptolepine". supporting information. . Retrieved 2021/09/14.
• 6、 Khaikate, Onnicha,Inthalaeng, Natthamon,Meesin, Jatuporn,Kantarod, Kritchasorn,Pohmakotr, Manat,Reutrakul, Vichai,Soorukram, Darunee,Leowanawat, Pawaret,Kuhakarn, Chutima. "Synthesis of Indolo-and Benzothieno[2,3-b]quinolines by a Cascade Cyclization of o-Alkynylisocyanobenzene Derivatives". . . Retrieved 2019/11/29.