2-[4-(2-Azido-phenyl)-6-(2-hydroxy-ethyl)-8-oxo-5,6,7,8-tetrahydro-quinolin-7-ylsulfanyl]-acetamide

Base Information

• Chemical Name: 2-[4-(2-Azido-phenyl)-6-(2-hydroxy-ethyl)-8-oxo-5,6,7,8-tetrahydro-quinolin-7-ylsulfanyl]-acetamide
• CAS No.: 165675-09-2
• Molecular Formula: C₁₉H₁₉N₅O₃S
• Molecular Weight: 397.458

Synonyms:2-[4-(2-Azido-phenyl)-6-(2-hydroxy-ethyl)-8-oxo-5,6,7,8-tetrahydro-quinolin-7-ylsulfanyl]-acetamide

Chemical Property of 2-[4-(2-Azido-phenyl)-6-(2-hydroxy-ethyl)-8-oxo-5,6,7,8-tetrahydro-quinolin-7-ylsulfanyl]-acetamide

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Technology Process of 2-[4-(2-Azido-phenyl)-6-(2-hydroxy-ethyl)-8-oxo-5,6,7,8-tetrahydro-quinolin-7-ylsulfanyl]-acetamide

There total 4 articles about 2-[4-(2-Azido-phenyl)-6-(2-hydroxy-ethyl)-8-oxo-5,6,7,8-tetrahydro-quinolin-7-ylsulfanyl]-acetamide 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: 91.0%

[6-(2-Acetoxy-ethyl)-4-(2-azido-phenyl)-8-oxo-5,6,7,8-tetrahydro-quinolin-7-ylsulfanyl]-acetic acid methyl ester → 2-[4-(2-Azido-phenyl)-6-(2-hydroxy-ethyl)-8-oxo-5,6,7,8-tetrahydro-quinolin-7-ylsulfanyl]-acetamide (165675-09-2)

Guidance literature:

With ammonia; In methanol; Ambient temperature;

DOI:10.1021/ja00155a010

Reference yield: 91.0%

2,6-bis(2-azidobenzylidene)-4-(2-hydroxyethyl)cyclohexanone (128350-17-4) → 2-[4-(2-Azido-phenyl)-6-(2-hydroxy-ethyl)-8-oxo-5,6,7,8-tetrahydro-quinolin-7-ylsulfanyl]-acetamide (165675-09-2)

Guidance literature:

With ammonia; potassium carbonate; In methanol; 1.) r.t., 12 h;

DOI:10.1016/00404-0399(50)08487-

Reference yield:

6-(2-acetoxyethyl)-4-(2-azidophenyl)-5,6,7,8-tetrahydroquinolin-8-one (135761-80-7) → 2-[4-(2-Azido-phenyl)-6-(2-hydroxy-ethyl)-8-oxo-5,6,7,8-tetrahydro-quinolin-7-ylsulfanyl]-acetamide (165675-09-2)

Guidance literature:

Multi-step reaction with 3 steps

1: pyridinium tribromide / acetic acid / 2 h / 50 °C

2: 66 percent / diisopropylethylamine / ethanol / 0.17 h / Ambient temperature

3: 91 percent / NH₃ / methanol / Ambient temperature

With ammonia; pyridinium hydrobromide perbromide; N-ethyl-N,N-diisopropylamine; In methanol; ethanol; acetic acid;

DOI:10.1021/ja00155a010

upstream raw materials:

2,6-bis(2-azidobenzylidene)-4-(2-hydroxyethyl)cyclohexanone

6-(2-acetoxyethyl)-4-(2-azidophenyl)-5,6,7,8-tetrahydroquinolin-8-one

Acetic acid 2-[4-(2-azido-phenyl)-7-bromo-8-oxo-5,6,7,8-tetrahydro-quinolin-6-yl]-ethyl ester

Downstream raw materials:

8-(2-Azido-phenyl)-10-(2-hydroxy-ethyl)-9,10-dihydro-4H-1-thia-4,5-diaza-phenanthren-3-one

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