4-(2-azidophenyl)-6-(2-(3-methylbut-2-enoylamino)ethyl)-5,6,7,8-tetrahydroquinolin-8-one ethylene ketal

Base Information

• Chemical Name: 4-(2-azidophenyl)-6-(2-(3-methylbut-2-enoylamino)ethyl)-5,6,7,8-tetrahydroquinolin-8-one ethylene ketal
• CAS No.: 135761-89-6
• Molecular Formula: C₂₄H₂₇N₅O₃
• Molecular Weight: 433.51
• Mol file: 135761-89-6.mol

Synonyms:4-(2-azidophenyl)-6-(2-(3-methylbut-2-enoylamino)ethyl)-5,6,7,8-tetrahydroquinolin-8-one ethylene ketal

Chemical Property of 4-(2-azidophenyl)-6-(2-(3-methylbut-2-enoylamino)ethyl)-5,6,7,8-tetrahydroquinolin-8-one ethylene ketal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-(2-azidophenyl)-6-(2-(3-methylbut-2-enoylamino)ethyl)-5,6,7,8-tetrahydroquinolin-8-one ethylene ketal

There total 15 articles about 4-(2-azidophenyl)-6-(2-(3-methylbut-2-enoylamino)ethyl)-5,6,7,8-tetrahydroquinolin-8-one ethylene ketal 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: 70.0%

3,3-Dimethylacryloyl chloride (3350-78-5) + 4-(2-azidophenyl)-6-(2-aminoethyl)-5,6,7,8-tetrahydroquinolin-8-one ethylene ketal (135761-88-5) → 4-(2-azidophenyl)-6-(2-(3-methylbut-2-enoylamino)ethyl)-5,6,7,8-tetrahydroquinolin-8-one ethylene ketal (135761-89-6)

Guidance literature:

With triethylamine; In tetrahydrofuran; at 0 - 20 ℃;

DOI:10.1021/ja00021a031

Reference yield:

cyclohexanedione monoethylene ketal (4746-97-8) → 4-(2-azidophenyl)-6-(2-(3-methylbut-2-enoylamino)ethyl)-5,6,7,8-tetrahydroquinolin-8-one ethylene ketal (135761-89-6)

Guidance literature:

Multi-step reaction with 15 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

10: 90 percent / HC(OEt)3, camphorsulfonic acid / 72 h / 60 °C

11: 99 percent / K₂CO₃ / methanol / 1.5 h / Ambient temperature

12: 100 percent / Et₃N / CH₂Cl₂ / 0 °C

13: 90 percent / dimethylformamide / 18 h / 50 °C

14: 90 percent / hydrazine hydrate / methanol / 3 h / 45 °C

15: 70 percent / Et₃N / tetrahydrofuran / 0 - 20 °C

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; camphor-10-sulfonic acid; hydroxylamine hydrochloride; potassium tert-butylate; hydrogen; potassium carbonate; ozone; hydrazine hydrate; triethylamine; orthoformic acid triethyl ester; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/ja00021a031

Reference yield:

ethyl 1,4-dioxaspiro[4,5]dec-8-ylideneacetate (51656-91-8) → 4-(2-azidophenyl)-6-(2-(3-methylbut-2-enoylamino)ethyl)-5,6,7,8-tetrahydroquinolin-8-one ethylene ketal (135761-89-6)

Guidance literature:

Multi-step reaction with 14 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

9: 90 percent / HC(OEt)3, camphorsulfonic acid / 72 h / 60 °C

10: 99 percent / K₂CO₃ / methanol / 1.5 h / Ambient temperature

11: 100 percent / Et₃N / CH₂Cl₂ / 0 °C

12: 90 percent / dimethylformamide / 18 h / 50 °C

13: 90 percent / hydrazine hydrate / methanol / 3 h / 45 °C

14: 70 percent / Et₃N / tetrahydrofuran / 0 - 20 °C

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; camphor-10-sulfonic acid; hydroxylamine hydrochloride; hydrogen; potassium carbonate; ozone; hydrazine hydrate; triethylamine; orthoformic acid triethyl ester; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/ja00021a031

upstream raw materials:

3,3-Dimethylacryloyl chloride

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

cyclohexanedione monoethylene ketal

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

Downstream raw materials:

cystodytin A

4-(2-azidophenyl)-6-<2-<(3-methylbut-2-enoyl)amino>ethyl>-5,6,7,8-tetrahydroquinolin-8-one