(E)-methyl 3-(1-methoxy-3-(p-tolyl)-1H-pyrano[4,3-b]quinolin-4-yl)acrylate

Base Information

• Chemical Name: (E)-methyl 3-(1-methoxy-3-(p-tolyl)-1H-pyrano[4,3-b]quinolin-4-yl)acrylate
• CAS No.: 1320362-49-9
• Molecular Formula: C₂₄H₂₁NO₄
• Molecular Weight: 387.435
• Mol file: 1320362-49-9.mol

Synonyms:(E)-methyl 3-(1-methoxy-3-(p-tolyl)-1H-pyrano[4,3-b]quinolin-4-yl)acrylate

Chemical Property of (E)-methyl 3-(1-methoxy-3-(p-tolyl)-1H-pyrano[4,3-b]quinolin-4-yl)acrylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-methyl 3-(1-methoxy-3-(p-tolyl)-1H-pyrano[4,3-b]quinolin-4-yl)acrylate

There total 4 articles about (E)-methyl 3-(1-methoxy-3-(p-tolyl)-1H-pyrano[4,3-b]quinolin-4-yl)acrylate 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: 80.0%

4-iodo-1-methoxy-3-(p-tolyl)-1H-pyrano[4,3-b]quinoline (1256286-01-7) + acrylic acid methyl ester (292638-85-8,9003-21-8,96-33-3) → (E)-methyl 3-(1-methoxy-3-(p-tolyl)-1H-pyrano[4,3-b]quinolin-4-yl)acrylate (1320362-49-9)

Guidance literature:

With trans-bis(triphenylphosphine)palladium dichloride; potassium carbonate; In N,N-dimethyl-formamide; at 120 ℃; for 2h; Inert atmosphere;

DOI:10.1021/co200100z

Reference yield:

2-chloro-3-quinoline carboxaldehyde (73568-25-9) → (E)-methyl 3-(1-methoxy-3-(p-tolyl)-1H-pyrano[4,3-b]quinolin-4-yl)acrylate (1320362-49-9)

Guidance literature:

Multi-step reaction with 3 steps

1: trans-bis(triphenylphosphine)palladium dichloride; triethylamine / 60 °C

2: iodine; potassium carbonate / dichloromethane / 2 h / 20 °C

3: trans-bis(triphenylphosphine)palladium dichloride; potassium carbonate / N,N-dimethyl-formamide / 2 h / 120 °C / Inert atmosphere

With trans-bis(triphenylphosphine)palladium dichloride; iodine; potassium carbonate; triethylamine; In dichloromethane; N,N-dimethyl-formamide; 1: Sonogashira coupling / 3: Heck reaction;

DOI:10.1021/co200100z

Reference yield:

2-(2-(p-tolyl)ethynyl)quinoline-3-carbaldehyde (1159765-59-9) → (E)-methyl 3-(1-methoxy-3-(p-tolyl)-1H-pyrano[4,3-b]quinolin-4-yl)acrylate (1320362-49-9)

Guidance literature:

Multi-step reaction with 2 steps

1: iodine; potassium carbonate / dichloromethane / 2 h / 20 °C

2: trans-bis(triphenylphosphine)palladium dichloride; potassium carbonate / N,N-dimethyl-formamide / 2 h / 120 °C / Inert atmosphere

With trans-bis(triphenylphosphine)palladium dichloride; iodine; potassium carbonate; In dichloromethane; N,N-dimethyl-formamide; 2: Heck reaction;

DOI:10.1021/co200100z

upstream raw materials:

2-(2-(p-tolyl)ethynyl)quinoline-3-carbaldehyde

4-iodo-1-methoxy-3-(p-tolyl)-1H-pyrano[4,3-b]quinoline

acrylic acid methyl ester

2-chloro-3-quinoline carboxaldehyde