allyl 3-(1-acetoxyethyl)-6-methoxy-4-methyl-2-(2-phenylethynyl)quinoline-1(2H)-carboxylate

Base Information

• Chemical Name: allyl 3-(1-acetoxyethyl)-6-methoxy-4-methyl-2-(2-phenylethynyl)quinoline-1(2H)-carboxylate
• CAS No.: 1335060-69-9
• Molecular Formula: C₂₇H₂₇NO₅
• Molecular Weight: 445.515
• Mol file: 1335060-69-9.mol

Synonyms:allyl 3-(1-acetoxyethyl)-6-methoxy-4-methyl-2-(2-phenylethynyl)quinoline-1(2H)-carboxylate

Chemical Property of allyl 3-(1-acetoxyethyl)-6-methoxy-4-methyl-2-(2-phenylethynyl)quinoline-1(2H)-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of allyl 3-(1-acetoxyethyl)-6-methoxy-4-methyl-2-(2-phenylethynyl)quinoline-1(2H)-carboxylate

There total 10 articles about allyl 3-(1-acetoxyethyl)-6-methoxy-4-methyl-2-(2-phenylethynyl)quinoline-1(2H)-carboxylate 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: 88.0%

1-(6-methoxy-4-methylquinolin-3-yl)ethyl acetate (1335060-64-4) + phenylacetylene (536-74-3) + Allyl chloroformate (2937-50-0) → allyl 3-(1-acetoxyethyl)-6-methoxy-4-methyl-2-(2-phenylethynyl)quinoline-1(2H)-carboxylate (1335060-69-9)

Guidance literature:

phenylacetylene; With isopropylmagnesium chloride; In tetrahydrofuran; at 0 - 20 ℃;

1-(6-methoxy-4-methylquinolin-3-yl)ethyl acetate; Allyl chloroformate; In tetrahydrofuran; at -18 - 20 ℃; diastereoselective reaction;

DOI:10.1016/j.tet.2011.07.090

Reference yield:

1-(6-methoxy-4-methylquinolin-3-yl)ethanol (1335060-55-3) → allyl 3-(1-acetoxyethyl)-6-methoxy-4-methyl-2-(2-phenylethynyl)quinoline-1(2H)-carboxylate (1335060-69-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: dmap; triethylamine / dichloromethane / 20 °C

2.1: isopropylmagnesium chloride / tetrahydrofuran / 0 - 20 °C

2.2: -18 - 20 °C

With dmap; isopropylmagnesium chloride; triethylamine; In tetrahydrofuran; dichloromethane; 2.1: Reissert type reaction / 2.2: Reissert type reaction;

DOI:10.1016/j.tet.2011.07.090

Reference yield:

2-{[(benzyloxy)carbonyl]amino}-5-hydroxybenzoic acid (214957-88-7) → allyl 3-(1-acetoxyethyl)-6-methoxy-4-methyl-2-(2-phenylethynyl)quinoline-1(2H)-carboxylate (1335060-69-9)

Guidance literature:

Multi-step reaction with 9 steps

1.1: potassium carbonate / acetone / 4 h / Reflux

2.1: n-butyllithium / tetrahydrofuran; hexane / 4 h / -78 °C

2.2: 20 °C

3.1: tetrahydrofuran / -78 - 20 °C

4.1: palladium on activated charcoal; hydrogen / ethyl acetate / 18 h / 20 °C

5.1: tetrahydrofuran / 24 h / 65 °C / Sealed tube

6.1: potassium carbonate / methanol / 22 h / 20 - 65 °C / Sealed tube

7.1: sodium tetrahydroborate / methanol / 0.25 h / 0 °C

8.1: dmap; triethylamine / dichloromethane / 20 °C

9.1: isopropylmagnesium chloride / tetrahydrofuran / 0 - 20 °C

9.2: -18 - 20 °C

With dmap; sodium tetrahydroborate; n-butyllithium; palladium on activated charcoal; hydrogen; isopropylmagnesium chloride; potassium carbonate; triethylamine; In tetrahydrofuran; methanol; hexane; dichloromethane; ethyl acetate; acetone; 9.1: Reissert type reaction / 9.2: Reissert type reaction;

DOI:10.1016/j.tet.2011.07.090

upstream raw materials:

2-{[(benzyloxy)carbonyl]amino}-5-hydroxybenzoic acid

1-(6-methoxy-4-methylquinolin-3-yl)ethanol

1-(6-methoxy-4-methylquinolin-3-yl)ethyl acetate

phenylacetylene

Refernces