1-(6-methoxy-3,4-dihydroquinolin-1(2H)-yl)prop-2-en-1-one

Base Information

• Chemical Name: 1-(6-methoxy-3,4-dihydroquinolin-1(2H)-yl)prop-2-en-1-one
• CAS No.: 91957-45-8
• Molecular Formula: C13H15 N O2
• Molecular Weight: 217.2637
• Mol file: 91957-45-8.mol

Synonyms:Quinoline,1-acryloyl-1,2,3,4-tetrahydro-6-methoxy- (7CI); NSC 79483

Chemical Property of 1-(6-methoxy-3,4-dihydroquinolin-1(2H)-yl)prop-2-en-1-one

Chemical Property:

• Vapor Pressure: 4.7E-05mmHg at 25°C
• Boiling Point: 349.4°Cat760mmHg
• Flash Point: 165.1°C
• Density: 1.118g/cm³

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1-(6-methoxy-3,4-dihydroquinolin-1(2H)-yl)prop-2-en-1-one

There total 5 articles about 1-(6-methoxy-3,4-dihydroquinolin-1(2H)-yl)prop-2-en-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: 93.3%

6-methoxy-1,2,3,4-tetrahydroquinoline (120-15-0) + 3-chloroprop-1-ene (107-05-1) → 1-(6-methoxy-3,4-dihydroquinolin-1(2H)-yl)prop-2-en-1-one (91957-45-8)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; for 3h; Cooling with ice;

Reference yield: 80.0%

6-methoxy-1,2,3,4-tetrahydroquinoline (120-15-0) + acryloyl chloride (814-68-6,25189-84-8) → 1-(6-methoxy-3,4-dihydroquinolin-1(2H)-yl)prop-2-en-1-one (91957-45-8)

Guidance literature:

6-methoxy-1,2,3,4-tetrahydroquinoline; With triethylamine; In dichloromethane; at 0 ℃; for 0.25h; Inert atmosphere;

acryloyl chloride; In dichloromethane; at 0 - 20 ℃; for 3h; Inert atmosphere;

DOI:10.1016/j.tetlet.2021.152861

Reference yield:

6-methoxy-2-oxo-1,2,3,4-tetrahydroquinoline (54197-64-7) → 1-(6-methoxy-3,4-dihydroquinolin-1(2H)-yl)prop-2-en-1-one (91957-45-8)

Guidance literature:

Multi-step reaction with 2 steps

1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / Reflux

2: N-ethyl-N,N-diisopropylamine / dichloromethane / 3 h / Cooling with ice

With lithium aluminium tetrahydride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane;

upstream raw materials:

6-methoxy-2-oxo-1,2,3,4-tetrahydroquinoline

6-methoxy-1,2,3,4-tetrahydroquinoline

3-chloroprop-1-ene

3,4-dihydro-6-hydroxy-2(1H)-quinolinone