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

Base Information

• Chemical Name: 6-(2-acetoxyethyl)-4-(2-azidophenyl)-5,6,7,8-tetrahydroquinolin-8-one
• CAS No.: 135761-80-7
• Molecular Formula: C₁₉H₁₈N₄O₃
• Molecular Weight: 350.377
• Mol file: 135761-80-7.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 13 articles about 6-(2-acetoxyethyl)-4-(2-azidophenyl)-5,6,7,8-tetrahydroquinolin-8-one 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:

cyclohexanedione monoethylene ketal (4746-97-8) → 6-(2-acetoxyethyl)-4-(2-azidophenyl)-5,6,7,8-tetrahydroquinolin-8-one (135761-80-7)

Guidance literature:

Multi-step reaction with 9 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

9: 1.) O₃, 2.) Me₂S / 1.) MeOH, -78 deg C, 2.) MeOH, from -78 deg C to RT, 1.5 h

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

DOI:10.1021/ja00021a031

Reference yield:

ethyl 1,4-dioxaspiro[4,5]dec-8-ylideneacetate (51656-91-8) → 6-(2-acetoxyethyl)-4-(2-azidophenyl)-5,6,7,8-tetrahydroquinolin-8-one (135761-80-7)

Guidance literature:

Multi-step reaction with 8 steps

1: 100 percent / H₂ / 10percent Pd/C / ethanol / 0.33 h / 108601 Torr / Ambient temperature

2: 90 percent / LAH / diethyl ether / -20 °C

3: 99 percent / aq. HCl / tetrahydrofuran

4: 88 percent / aq. NaOH / ethanol / 0.5 h / Ambient temperature

5: 99 percent / pyridine / Ambient temperature

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

7: 56 percent / hydroxylamine hydrochloride / acetonitrile / Heating

8: 1.) O₃, 2.) Me₂S / 1.) MeOH, -78 deg C, 2.) MeOH, from -78 deg C to RT, 1.5 h

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

DOI:10.1021/ja00021a031

Reference yield:

4-(2-acetoxyethyl)-2,6-bis(2-azidobenzylidene)cyclohexanone (128350-18-5) → 6-(2-acetoxyethyl)-4-(2-azidophenyl)-5,6,7,8-tetrahydroquinolin-8-one (135761-80-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) Yb(fod)3, 2.) HONH₂*HCl / 1.) CH₂Cl₂, reflux, 2.) CH₃CN, reflux

2: 1.) O₃, 2.) Me₂S / 1.) CH₂Cl₂, CH₃OH, -78 deg C, 2.) CH₂Cl₂, CH₃OH, -78 deg C to RT

With tris(6,6,7,7,8,8,8-heptafluoro-2,2-dimethyl-3,5-octanedionato)ytterbium; dimethylsulfide; hydroxylamine hydrochloride; ozone;

DOI:10.1021/ja00051a062

upstream raw materials:

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

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

cyclohexanedione monoethylene ketal

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

Downstream raw materials:

Acetic acid 6-(2-acetoxy-ethyl)-4-(2-azido-phenyl)-quinolin-8-yl ester

Acetic acid 6-(2-acetoxy-ethyl)-4-(2-azido-phenyl)-5,6-dihydro-quinolin-8-yl ester

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

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