3-Ethyl-2,2-diMethyl-1,2,3,4-tetrahydroquinoline

Base Information

• Chemical Name: 3-Ethyl-2,2-diMethyl-1,2,3,4-tetrahydroquinoline
• CAS No.: 179899-03-7
• Molecular Formula: C13H19N
• Molecular Weight: 189.29700
• Mol file: 179899-03-7.mol

Synonyms:(R/S)-3-ethyl-1,2,3,4,-tetrahydro-2,2-dimethylquinoline;3-Ethyl-2,2-dimethyl-1,2,3,4-tetrahydro-quinoline;3-ethyl-1,2,3,4-tetrahydro-2,2-dimethylquinoline;(R/S)-3-Ethyl-1,2,3,4tetrahydro-2,2-dimethylquinoline;

Chemical Property of 3-Ethyl-2,2-diMethyl-1,2,3,4-tetrahydroquinoline

Chemical Property:

• PSA: 12.03000
• LogP: 3.59740

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-Ethyl-2,2-diMethyl-1,2,3,4-tetrahydroquinoline

There total 7 articles about 3-Ethyl-2,2-diMethyl-1,2,3,4-tetrahydroquinoline 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:

Et3 SiH + BF3 -OEt2 + 2-quinolone (59-31-4,70254-42-1,493-62-9) → (R/S)-3-ethyl-1,2,3,4-tetrahydro-2,2-dimethylquinoline (179899-03-7)

Guidance literature:

In dichloromethane;

Reference yield:

2,2-dimethyl-1,2-dihydroquinoline (14465-61-3) → (R/S)-3-ethyl-1,2,3,4-tetrahydro-2,2-dimethylquinoline (179899-03-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) n-butyllithium / 1.) Et₂O, hexane, -65 deg C, 10 min, 2.) Et₂O, hexane, RT, 2 h

2: 1.) BHF*THF, 2.) aq. KOH, 30percent aq. H₂O₂ / 1.) THF, RT, 5 h, 2.) THF, 60 min

3: 88 percent / PCC / CH₂Cl₂ / 3 h / Ambient temperature

4: 1.) NaH, 2.) TFA 3.) Et₃SiH, BF₃*OEt₂

With triethylsilane; potassium hydroxide; n-butyllithium; BHF*THF; boron trifluoride diethyl etherate; dihydrogen peroxide; sodium hydride; pyridinium chlorochromate; trifluoroacetic acid; In dichloromethane;

DOI:10.1021/jm970699s

Reference yield:

3-methyl-3-phenylamino-1-butyne (7471-09-2) → (R/S)-3-ethyl-1,2,3,4-tetrahydro-2,2-dimethylquinoline (179899-03-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 74 percent / CuCl / tetrahydrofuran / 14 h / Heating

2: 1.) n-butyllithium / 1.) Et₂O, hexane, -65 deg C, 10 min, 2.) Et₂O, hexane, RT, 2 h

3: 1.) BHF*THF, 2.) aq. KOH, 30percent aq. H₂O₂ / 1.) THF, RT, 5 h, 2.) THF, 60 min

4: 88 percent / PCC / CH₂Cl₂ / 3 h / Ambient temperature

5: 1.) NaH, 2.) TFA 3.) Et₃SiH, BF₃*OEt₂

With triethylsilane; potassium hydroxide; n-butyllithium; BHF*THF; boron trifluoride diethyl etherate; dihydrogen peroxide; sodium hydride; pyridinium chlorochromate; trifluoroacetic acid; copper(l) chloride; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jm970699s

upstream raw materials:

ethyl iodide

1-tert-butoxycarbonyl-1,2,3,4-tetrahydro-2,2-dimethyl-4-quinolinone

2,2-dimethyl-1,2-dihydroquinoline

3-methyl-3-phenylamino-1-butyne