3-methyl-2,3,4,9-tetrahydro-1H-carbazole

Base Information

• Chemical Name: 3-methyl-2,3,4,9-tetrahydro-1H-carbazole
• CAS No.: 100986-21-8
• Molecular Formula: C₁₃H₁₅N
• Molecular Weight: 185.269
• Mol file: 100986-21-8.mol

Synonyms:

Chemical Property of 3-methyl-2,3,4,9-tetrahydro-1H-carbazole

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-methyl-2,3,4,9-tetrahydro-1H-carbazole

There total 21 articles about 3-methyl-2,3,4,9-tetrahydro-1H-carbazole 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: 99.0%

1-methylcyclohexan-4-one (589-92-4) + phenylhydrazine (100-63-0) → 3-methyl-2,3,4,9-tetrahydro-1H-carbazole (6933-54-6,100986-21-8)

Guidance literature:

With trichloroacetic acid; at 100 ℃; for 0.0833333h;

DOI:10.1515/HC.2003.9.1.9

Reference yield: 95.0%

3-methyl-1,2,3,4,4a,9a-hexahydro-carbazole (6731-87-9) → 3-methyl-2,3,4,9-tetrahydro-1H-carbazole (6933-54-6,100986-21-8)

Guidance literature:

With trimethylamine-N-oxide; Co(salophen)-HQ; In methanol; at 80 ℃; for 16h; Sealed tube; Green chemistry;

DOI:10.1002/chem.202102483

Reference yield: 92.0%

di-tert-butyl 1-(4-methylcyclohex-1-en-1-yl)-2-phenylhydrazine-1,2-dicarboxylate → 3-methyl-2,3,4,9-tetrahydro-1H-carbazole (6933-54-6,100986-21-8)

Guidance literature:

With zinc(II) chloride; In 1,4-dioxane; at 20 - 90 ℃; for 1h; regioselective reaction; Sealed tube; Inert atmosphere;

DOI:10.1021/ol502031q

upstream raw materials:

4-methyl-cyclohexanone-phenylhydrazone

acetic acid

1-methylcyclohexan-4-one

phenylhydrazine

Downstream raw materials:

9H-carbazole-3-carbaldehyde

3-Methyl-9H-carbazole

1-methoxy-3-methylcarbazole

1-hydroxy-3-methyl-9H-carbazole

Refernces

• 1、 Kapoor, Kamal K.,Ganai, Bilal A.,Kumar, Satish,Andotra, Charanjeet S.. "KHSO4 · H2O/SiO2-catalyzed, one-pot, solvent-free synthesis of pyrazolines, tetrahydrocarbozoles and indoles using microwave irradiation". . p. 2727 - 2735. Retrieved 2006.
• 2、 Li, Bai Lin,Zhong, Ai Guo,Xu, Dan-Qian. "Novel SO3H-functionalized ionic liquids catalyzed a simple, green and efficient procedure for Fischer indole synthesis in water under microwave irradiation". . p. 45 - 50,6. Retrieved 2012.
• 3、 Matsumoto, Kiyoshi,Tanaka, Akinori,Yukio, Ikemi,Hayashi, Naoto,Toda, Mitsuo,Bulman, Robert A.. "Fischer indole synthesis in the absence of a solvent". . p. 9 - 12. Retrieved 2003.
• 4、 Qiu, Yichen,Puni, Kararaina Te,Duplan, Clotilde C.,Lindsay, Ashley C.,Sperry, Jonathan. "Tetrahydrocarbazoles by mechanochemical Fischer indolisation". supporting information. . Retrieved 2021/05/26.
• 5、 Yan, Qiao,Gin, Emma,Wasinska-Kalwa, Malgorzata,Banwell, Martin G.,Carr, Paul D.. "A Palladium-Catalyzed Ullmann Cross-Coupling/Reductive Cyclization Route to the Carbazole Natural Products 3-Methyl-9H-carbazole, Glycoborine, Glycozoline, Clauszoline K, Mukonine, and Karapinchamine A". . p. 4148 - 4159. Retrieved 2017/04/27.