methyl 4-methoxy-8-[1-phenoxyethyl]quinoline-2-carboxylate

Base Information

• Chemical Name: methyl 4-methoxy-8-[1-phenoxyethyl]quinoline-2-carboxylate
• CAS No.: 1644185-87-4
• Molecular Formula: C₂₀H₁₉NO₄
• Molecular Weight: 337.375
• Mol file: 1644185-87-4.mol

Synonyms:methyl 4-methoxy-8-[1-phenoxyethyl]quinoline-2-carboxylate

Chemical Property of methyl 4-methoxy-8-[1-phenoxyethyl]quinoline-2-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 4-methoxy-8-[1-phenoxyethyl]quinoline-2-carboxylate

There total 3 articles about methyl 4-methoxy-8-[1-phenoxyethyl]quinoline-2-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: 55.0%

methyl 8-(1-hydroxyethyl)-4-methoxyquinoline-2-carboxylate (1644185-86-3) + phenol (108-95-2,27073-41-2) → methyl 4-methoxy-8-[1-phenoxyethyl]quinoline-2-carboxylate (1644185-87-4)

Guidance literature:

With di-tert-butyl-diazodicarboxylate; In toluene; at 80 ℃; for 3h; Inert atmosphere;

DOI:10.1002/ejoc.201402247

Reference yield:

methyl 8-acetyl-4-methoxyquinoline-2-carboxylate (1644185-85-2) → methyl 4-methoxy-8-[1-phenoxyethyl]quinoline-2-carboxylate (1644185-87-4)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium tetrahydroborate / 1,2-dichloro-ethane / 8 h / 55 °C

2: di-tert-butyl-diazodicarboxylate / toluene / 3 h / 80 °C / Inert atmosphere

With sodium tetrahydroborate; di-tert-butyl-diazodicarboxylate; In 1,2-dichloro-ethane; toluene; 2: |Mitsunobu Displacement;

DOI:10.1002/ejoc.201402247

Reference yield:

methyl 8-acetyl-4-hydroxyquinoline-2-carboxylate (10037-32-8) → methyl 4-methoxy-8-[1-phenoxyethyl]quinoline-2-carboxylate (1644185-87-4)

Guidance literature:

Multi-step reaction with 3 steps

1: potassium carbonate / acetone / 1 h / Reflux

2: sodium tetrahydroborate / 1,2-dichloro-ethane / 8 h / 55 °C

3: di-tert-butyl-diazodicarboxylate / toluene / 3 h / 80 °C / Inert atmosphere

With sodium tetrahydroborate; di-tert-butyl-diazodicarboxylate; potassium carbonate; In 1,2-dichloro-ethane; acetone; toluene; 3: |Mitsunobu Displacement;

DOI:10.1002/ejoc.201402247

upstream raw materials:

methyl 8-acetyl-4-hydroxyquinoline-2-carboxylate

methyl 8-acetyl-4-methoxyquinoline-2-carboxylate

methyl 8-(1-hydroxyethyl)-4-methoxyquinoline-2-carboxylate

phenol

Downstream raw materials:

methyl (1S)-4-methoxy-8-[1-phenoxyethyl]quinoline-2-carboxylate

methyl (1R)-4-methoxy-8-[1-phenoxyethyl]quinoline-2-carboxylate