4,4-dimethyl-1,2,3,4-tetra-hydroisoquinolin-1-one

Base Information

• Chemical Name: 4,4-dimethyl-1,2,3,4-tetra-hydroisoquinolin-1-one
• CAS No.: 27295-88-1
• Molecular Formula: C₁₁H₁₃NO
• Molecular Weight: 175.23
• Mol file: 27295-88-1.mol

Synonyms:

Chemical Property of 4,4-dimethyl-1,2,3,4-tetra-hydroisoquinolin-1-one

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

4,4-dimethyl-1,2,3,4-tetrahydroisoquinolin-1-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4,4-dimethyl-1,2,3,4-tetra-hydroisoquinolin-1-one

There total 12 articles about 4,4-dimethyl-1,2,3,4-tetra-hydroisoquinolin-1-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: 92.0%

tert-butyl 4,4-dimethyl-1-oxo-3,4-dihydroisoquinoline-2(1H)-carboxylate → 4,4-dimethyl-1,2,3,4-tetra-hydroisoquinolin-1-one (27295-88-1)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 23 ℃; for 1h;

DOI:10.1021/jacs.8b03187

Reference yield: 46.0%

3,3-dimethylindan-1-one (26465-81-6) → 4,4-dimethyl-3,4-dihydro-1H-quinolin-2-one (76693-04-4) + 4,4-dimethyl-1,2,3,4-tetra-hydroisoquinolin-1-one (27295-88-1)

Guidance literature:

With sodium azide; methanesulfonic acid; at 0 ℃; for 3h; Inert atmosphere; Heating;

DOI:10.2174/1570178614666171129163540

Reference yield:

2-methyl-2-phenylpropionic acid (826-55-1) → 4,4-dimethyl-1,2,3,4-tetra-hydroisoquinolin-1-one (27295-88-1)

Guidance literature:

Multi-step reaction with 7 steps

1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 2 h / 23 °C

2: ammonia / ethyl acetate / 0.25 h / 23 °C

3: sulfuric acid; acetic acid / 16 h / Reflux

4: lithium aluminium tetrahydride / tetrahydrofuran / 0 °C / Reflux; Inert atmosphere

5: potassium carbonate / water; tetrahydrofuran / 2 h / Reflux

6: 18-crown-6 ether; potassium permanganate / dichloromethane / 3 h / 0 - 23 °C

7: trifluoroacetic acid / dichloromethane / 1 h / 23 °C

With potassium permanganate; lithium aluminium tetrahydride; oxalyl dichloride; 18-crown-6 ether; sulfuric acid; ammonia; potassium carbonate; acetic acid; N,N-dimethyl-formamide; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; water; ethyl acetate; 3: |Pictet-Spengler Synthesis;

DOI:10.1021/jacs.8b03187

upstream raw materials:

2-methyl-2-phenylpropionic acid

2-methyl-2-phenylpropanoyl chloride

2-methyl-2-phenyl-propanamide

1,4-dihydro-2,4,4-trimethylisoquinolin-3(2H)-one

Refernces

• 1、 Arora, Rashi,Bala, Renu,Kumari, Poonam,Sood, Sumit,Yadav, Ajar Nath,Singh, Nasib,Singh, Karan. "Schmidt reaction on substituted 1-indanones / N-alkylation: Synthesis of benzofused six-membered ring lactams and their evaluation as antimicrobial agents". . p. 606 - 613. Retrieved 2019/05/01.
• 2、 -. "Antiserotonins, their preparation and pharmaceutical compositions containing them". . . Retrieved 2008/06/13.