1-ethyl-4-oxo-6-[3-({2-[(phenylmethyl)oxy]ethyl}oxy)-1-propyn-1-yl]-1,4-dihydro-3-quinolinecarboxylic acid

Base Information

• Chemical Name: 1-ethyl-4-oxo-6-[3-({2-[(phenylmethyl)oxy]ethyl}oxy)-1-propyn-1-yl]-1,4-dihydro-3-quinolinecarboxylic acid
• CAS No.: 869310-65-6
• Molecular Formula: C₂₄H₂₃NO₅
• Molecular Weight: 405.45
• Mol file: 869310-65-6.mol

Synonyms:1-ethyl-4-oxo-6-[3-({2-[(phenylmethyl)oxy]ethyl}oxy)-1-propyn-1-yl]-1,4-dihydro-3-quinolinecarboxylic acid

Chemical Property of 1-ethyl-4-oxo-6-[3-({2-[(phenylmethyl)oxy]ethyl}oxy)-1-propyn-1-yl]-1,4-dihydro-3-quinolinecarboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-ethyl-4-oxo-6-[3-({2-[(phenylmethyl)oxy]ethyl}oxy)-1-propyn-1-yl]-1,4-dihydro-3-quinolinecarboxylic acid

There total 8 articles about 1-ethyl-4-oxo-6-[3-({2-[(phenylmethyl)oxy]ethyl}oxy)-1-propyn-1-yl]-1,4-dihydro-3-quinolinecarboxylic acid 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: 82.0%

1-ethyl-6-iodo-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid (797052-44-9) + ({[2-(2-propyn-1-yloxy)ethyl]oxy}methyl)benzene (219716-49-1) → 1-ethyl-4-oxo-6-[3-({2-[(phenylmethyl)oxy]ethyl}oxy)-1-propyn-1-yl]-1,4-dihydro-3-quinolinecarboxylic acid (869310-65-6)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In acetonitrile; at 50 ℃; for 24h;

DOI:10.1016/j.bmc.2010.06.050

Reference yield:

({[2-(2-propyn-1-yloxy)ethyl]oxy}methyl)benzene (219716-49-1) → 1-ethyl-4-oxo-6-[3-({2-[(phenylmethyl)oxy]ethyl}oxy)-1-propyn-1-yl]-1,4-dihydro-3-quinolinecarboxylic acid (869310-65-6)

Guidance literature:

1-ethyl-6-iodo-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid; With copper(l) iodide; In water; acetonitrile; at 50 ℃; for 0.333333h;

({[2-(2-propyn-1-yloxy)ethyl]oxy}methyl)benzene; bis-triphenylphosphine-palladium(II) chloride; In water; acetonitrile; at 50 ℃;

Reference yield:

1-ethyl-6-iodo-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid ethyl ester (797041-75-9) → 1-ethyl-4-oxo-6-[3-({2-[(phenylmethyl)oxy]ethyl}oxy)-1-propyn-1-yl]-1,4-dihydro-3-quinolinecarboxylic acid (869310-65-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium hydroxide / ethanol; water / 0.58 h / 78 °C

1.2: 60 °C / pH 6

2.1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine / ethanol / 1.33 h / 57 °C

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; sodium hydroxide; In ethanol; water; 2.1: Sonogashira coupling;

DOI:10.1021/op100199t

upstream raw materials:

1-ethyl-6-iodo-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid

({[2-(2-propyn-1-yloxy)ethyl]oxy}methyl)benzene

2-fluoro-5-iodobenzoyl chloride

ethyl 3-(dimethylamino)-2-[(2-fluoro-5-iodophenyl)carbonyl]-2-propenoate

Downstream raw materials:

1-ethyl-4-oxo-6-[3-({2-[(phenylmethyl)oxy]ethyl}oxy)propyl]-1,4-dihydro-3-quinolinecarboxylic acid

C₁₅H₁₇NO₃