4-oxo-N-(pyridin-3-ylmethyl)-6-(o-tolyl)-1,4-dihydroquinoline-3-carboxamide

Base Information

Chemical Name:4-oxo-N-(pyridin-3-ylmethyl)-6-(o-tolyl)-1,4-dihydroquinoline-3-carboxamide
CAS No.:1449221-57-1
Molecular Formula:C₂₃H₁₉N₃O₂
Molecular Weight:369.423
Hs Code.:

Synonyms:4-oxo-N-(pyridin-3-ylmethyl)-6-(o-tolyl)-1,4-dihydroquinoline-3-carboxamide

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Chemical Property of 4-oxo-N-(pyridin-3-ylmethyl)-6-(o-tolyl)-1,4-dihydroquinoline-3-carboxamide

Chemical Property:

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Technology Process of 4-oxo-N-(pyridin-3-ylmethyl)-6-(o-tolyl)-1,4-dihydroquinoline-3-carboxamide

There total 4 articles about 4-oxo-N-(pyridin-3-ylmethyl)-6-(o-tolyl)-1,4-dihydroquinoline-3-carboxamide 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: 72.09%

: 3731-52-0
3-Aminomethylpyridine

: 1449221-76-4
4-oxo-6-(o-tolyl)-1,4-dihydroquinoline-3-carboxylic acid

: 1449221-57-1
4-oxo-N-(pyridin-3-ylmethyl)-6-(o-tolyl)-1,4-dihydroquinoline-3-carboxamide

Guidance literature:: 4-oxo-6-(o-tolyl)-1,4-dihydroquinoline-3-carboxylic acid; With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 0.25h; Inert atmosphere;

3-Aminomethylpyridine; In dichloromethane; at 20 ℃; for 12h; Inert atmosphere;
DOI:10.1016/j.ejmech.2014.04.025

Reference yield:

: 101937-44-4
diethyl 2-((4-bromophenylamino)methylene)malonate

: 1449221-57-1
4-oxo-N-(pyridin-3-ylmethyl)-6-(o-tolyl)-1,4-dihydroquinoline-3-carboxamide

Guidance literature:: Multi-step reaction with 4 steps

1.1: trichlorophosphate / water / 12 h / 20 - 70 °C

2.1: potassium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / water; tetrahydrofuran / 12 h / Reflux; Inert atmosphere

3.1: sodium hydroxide / water / 2 h / Reflux

4.1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 0.25 h / 20 °C / Inert atmosphere

4.2: 12 h / 20 °C / Inert atmosphere

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; sodium hydroxide; trichlorophosphate; In tetrahydrofuran; dichloromethane; water;
DOI:10.1016/j.ejmech.2014.04.025

Reference yield:

: 79607-23-1,122794-99-4
ethyl 6-bromo-4-oxo-1,4-dihydro-quinoline-3-carboxylate

: 1449221-57-1
4-oxo-N-(pyridin-3-ylmethyl)-6-(o-tolyl)-1,4-dihydroquinoline-3-carboxamide

Guidance literature:: Multi-step reaction with 3 steps

1.1: potassium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / water; tetrahydrofuran / 12 h / Reflux; Inert atmosphere

2.1: sodium hydroxide / water / 2 h / Reflux

3.1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 0.25 h / 20 °C / Inert atmosphere

3.2: 12 h / 20 °C / Inert atmosphere

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; sodium hydroxide; In tetrahydrofuran; dichloromethane; water;
DOI:10.1016/j.ejmech.2014.04.025