6-(2-acetoxyethyl)-8-(2-azidobenzylidene)-4-(2-azidophenyl)-5,6,7,8-tetrahydroquinoline

Base Information

• Chemical Name: 6-(2-acetoxyethyl)-8-(2-azidobenzylidene)-4-(2-azidophenyl)-5,6,7,8-tetrahydroquinoline
• CAS No.: 135761-79-4
• Molecular Formula: C₂₆H₂₃N₇O₂
• Molecular Weight: 465.514
• Mol file: 135761-79-4.mol

Synonyms:6-(2-acetoxyethyl)-8-(2-azidobenzylidene)-4-(2-azidophenyl)-5,6,7,8-tetrahydroquinoline

Chemical Property of 6-(2-acetoxyethyl)-8-(2-azidobenzylidene)-4-(2-azidophenyl)-5,6,7,8-tetrahydroquinoline

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6-(2-acetoxyethyl)-8-(2-azidobenzylidene)-4-(2-azidophenyl)-5,6,7,8-tetrahydroquinoline

There total 13 articles about 6-(2-acetoxyethyl)-8-(2-azidobenzylidene)-4-(2-azidophenyl)-5,6,7,8-tetrahydroquinoline 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: 77.0%

Acetic acid 2-{(2S,4R)-4-(2-azido-phenyl)-8-[1-(2-azido-phenyl)-meth-(E)-ylidene]-2-ethoxy-3,4,5,6,7,8-hexahydro-2H-chromen-6-yl}-ethyl ester → 6-(2-acetoxyethyl)-8-(2-azidobenzylidene)-4-(2-azidophenyl)-5,6,7,8-tetrahydroquinoline (135761-79-4)

Guidance literature:

With hydroxylamine hydrochloride; In acetonitrile; Heating;

DOI:10.1016/S0040-4039(01)93799-2

Reference yield: 56.0%

6-(2-acetoxyethyl)-8-(2-azidobenzylidene)-4-(2-azidophenyl)-2-ethoxy-3,4,5,6,7,8-hexahydro-2H-benzopyran → 6-(2-acetoxyethyl)-8-(2-azidobenzylidene)-4-(2-azidophenyl)-5,6,7,8-tetrahydroquinoline (135761-79-4)

Guidance literature:

With hydroxylamine hydrochloride; In acetonitrile; Heating;

DOI:10.1021/ja00021a031

Reference yield:

cyclohexanedione monoethylene ketal (4746-97-8) → 6-(2-acetoxyethyl)-8-(2-azidobenzylidene)-4-(2-azidophenyl)-5,6,7,8-tetrahydroquinoline (135761-79-4)

Guidance literature:

Multi-step reaction with 8 steps

1: 1.) t-BuOK / 1.) DME, from 0 deg C to RT, 2.) DME, RT

2: 100 percent / H₂ / 10percent Pd/C / ethanol / 0.33 h / 108601 Torr / Ambient temperature

3: 90 percent / LAH / diethyl ether / -20 °C

4: 99 percent / aq. HCl / tetrahydrofuran

5: 88 percent / aq. NaOH / ethanol / 0.5 h / Ambient temperature

6: 99 percent / pyridine / Ambient temperature

7: Yb(fod)3 / 1,2-dichloro-ethane / 24 h / Heating

8: 56 percent / hydroxylamine hydrochloride / acetonitrile / Heating

With pyridine; hydrogenchloride; sodium hydroxide; lithium aluminium tetrahydride; tris(6,6,7,7,8,8,8-heptafluoro-2,2-dimethyl-3,5-octanedionato)ytterbium; hydroxylamine hydrochloride; potassium tert-butylate; hydrogen; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; ethanol; 1,2-dichloro-ethane; acetonitrile;

DOI:10.1021/ja00021a031

upstream raw materials:

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

ethyl vinyl ether

cyclohexanedione monoethylene ketal

ethyl 1,4-dioxaspiro[4,5]dec-8-ylideneacetate

Downstream raw materials:

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

4-(2-azidophenyl)-6-(2-aminoethyl)-5,6,7,8-tetrahydroquinolin-8-one ethylene ketal

4-(2-azidophenyl)-6-(2-hydroxyethyl)-5,6,7,8-tetrahydroquinolin-8-one ethylene ketal