1-Boc-6-amino-4,4-dimethyl-3,4-dihydro-2H-quinoline

Base Information

• Chemical Name: 1-Boc-6-amino-4,4-dimethyl-3,4-dihydro-2H-quinoline
• CAS No.: 1187933-54-5
• Molecular Formula: C16H24N2O2
• Molecular Weight: 276.37
• Mol file: 1187933-54-5.mol

Synonyms:1-Boc-6-amino-4,4-dimethyl-3,4-dihydro-2H-quinoline;tert-Butyl 6-amino-4,4-dimethyl-3,4-dihydroquinoline-1(2H)-carboxylate

Chemical Property of 1-Boc-6-amino-4,4-dimethyl-3,4-dihydro-2H-quinoline

Chemical Property:

• PSA: 55.56000
• LogP: 4.33780

Purity/Quality:

98.5% ^*data from raw suppliers

1-Boc-6-amino-4,4-dimethyl-3,4-dihydro-2H-quinoline ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1-Boc-6-amino-4,4-dimethyl-3,4-dihydro-2H-quinoline

There total 7 articles about 1-Boc-6-amino-4,4-dimethyl-3,4-dihydro-2H-quinoline 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:

tert-butyl 6-azido-4,4-dimethyl-3,4-dihydroquinoline-1(2H)-carboxylate → tert-butyl 6-amino-4,4-dimethyl-3,4-dihydroquinoline-1(2H)-carboxylate (1187933-54-5)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; at 23 ℃; for 6h; under 760.051 Torr;

DOI:10.1016/j.bmc.2019.115244

Reference yield:

4-bromo-aniline (106-40-1) → tert-butyl 6-amino-4,4-dimethyl-3,4-dihydroquinoline-1(2H)-carboxylate (1187933-54-5)

Guidance literature:

Multi-step reaction with 6 steps

1.1: chloroform / 5 h / Reflux; Inert atmosphere

2.1: aluminum (III) chloride / 1,2-dichloro-ethane / 1 h / 83 °C / Inert atmosphere

3.1: dimethylsulfide borane complex / toluene / 3 h / 0 - 110 °C / Inert atmosphere

4.1: n-butyllithium / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

4.2: 18.5 h / -78 - 23 °C / Inert atmosphere

5.1: sodium azide; copper(l) iodide; L-proline; sodium hydroxide / 18 h / 90 °C / Sealed tube; Inert atmosphere

6.1: palladium 10% on activated carbon; hydrogen / methanol / 6 h / 23 °C / 760.05 Torr

With aluminum (III) chloride; copper(l) iodide; n-butyllithium; sodium azide; dimethylsulfide borane complex; palladium 10% on activated carbon; hydrogen; L-proline; sodium hydroxide; In tetrahydrofuran; methanol; chloroform; 1,2-dichloro-ethane; toluene; 2.1: |Friedel-Crafts Alkylation;

DOI:10.1016/j.bmc.2019.115244

Reference yield:

3,3-Dimethylacryloyl chloride (3350-78-5) → tert-butyl 6-amino-4,4-dimethyl-3,4-dihydroquinoline-1(2H)-carboxylate (1187933-54-5)

Guidance literature:

Multi-step reaction with 6 steps

1.1: chloroform / 5 h / Reflux; Inert atmosphere

2.1: aluminum (III) chloride / 1,2-dichloro-ethane / 1 h / 83 °C / Inert atmosphere

3.1: dimethylsulfide borane complex / toluene / 3 h / 0 - 110 °C / Inert atmosphere

4.1: n-butyllithium / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

4.2: 18.5 h / -78 - 23 °C / Inert atmosphere

5.1: sodium azide; copper(l) iodide; L-proline; sodium hydroxide / 18 h / 90 °C / Sealed tube; Inert atmosphere

6.1: palladium 10% on activated carbon; hydrogen / methanol / 6 h / 23 °C / 760.05 Torr

With aluminum (III) chloride; copper(l) iodide; n-butyllithium; sodium azide; dimethylsulfide borane complex; palladium 10% on activated carbon; hydrogen; L-proline; sodium hydroxide; In tetrahydrofuran; methanol; chloroform; 1,2-dichloro-ethane; toluene; 2.1: |Friedel-Crafts Alkylation;

DOI:10.1016/j.bmc.2019.115244

upstream raw materials:

4-bromo-aniline

3,3-Dimethylacryloyl chloride

N-(3,3'-dimethylacryoloyl)-4-bromoaniline

4,4-dimethyl-6-bromo-2-oxo-1,2,3,4-tetrahydroquinoline

Refernces

• 1、 -. "CHROMAN-SUBSTITUTED, TETRAHYDROQUINOLINE-SUBSTITUTED AND THIOCHROMAN-SUBSTITUTED HETEROAROTINOIDS AS ANTI-CANCER AGENTS". . . Retrieved 2020/03/09.