2(1H)-Quinolinone, 8-hydroxy-5-[2-[[2-(4-hydroxyphenyl)ethyl]amino]ethyl]-, monohydrobromide

Base Information

• Chemical Name: 2(1H)-Quinolinone, 8-hydroxy-5-[2-[[2-(4-hydroxyphenyl)ethyl]amino]ethyl]-, monohydrobromide
• CAS No.: 94592-43-5
• Molecular Formula: C19H20N2O3.BrH
• Molecular Weight: 405.291
• Mol file: 94592-43-5.mol

Synonyms:

Chemical Property of 2(1H)-Quinolinone, 8-hydroxy-5-[2-[[2-(4-hydroxyphenyl)ethyl]amino]ethyl]-, monohydrobromide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2(1H)-Quinolinone, 8-hydroxy-5-[2-[[2-(4-hydroxyphenyl)ethyl]amino]ethyl]-, monohydrobromide

There total 12 articles about 2(1H)-Quinolinone, 8-hydroxy-5-[2-[[2-(4-hydroxyphenyl)ethyl]amino]ethyl]-, monohydrobromide 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: 25.0%

5-<2-<<2-(4-methoxyphenyl)ethyl>amino>ethyl>-8-methoxycarbostyril (94592-40-2) → 8-hydroxy-5-<2-<<2-(4-hydroxyphenyl)ethyl>amino>ethyl>carbostyril hydrobromide (94592-43-5)

Guidance literature:

With boron tribromide; In dichloromethane; a) 25 deg C, 30 min, b) reflux, 1 h;

DOI:10.1021/jm00150a010

Reference yield:

3-(4-methoxyphenyl)-oxiranecarbonitrile (81860-68-6) → 8-hydroxy-5-<2-<<2-(4-hydroxyphenyl)ethyl>amino>ethyl>carbostyril hydrobromide (94592-43-5)

Guidance literature:

Multi-step reaction with 4 steps

1: conc.H₂SO₄ / 1.) water, reflux, 30 min, 2.) water

2: NaBH₄ / ethanol / 24 h / 25 °C

3: 73 percent / H₂, 12N HCl / Pd/C / H₂O; acetic acid / 0.5 h / 25 °C / 2585.7 Torr

4: 25 percent / BBr₃ / CH₂Cl₂ / a) 25 deg C, 30 min, b) reflux, 1 h

With hydrogenchloride; sodium tetrahydroborate; sulfuric acid; hydrogen; boron tribromide; palladium on activated charcoal; In ethanol; dichloromethane; water; acetic acid;

DOI:10.1021/jm00150a010

Reference yield:

2-(8-hydroxyquinolin-5-yl)acetonitrile (57434-83-0) → 8-hydroxy-5-<2-<<2-(4-hydroxyphenyl)ethyl>amino>ethyl>carbostyril hydrobromide (94592-43-5)

Guidance literature:

Multi-step reaction with 10 steps

1: 1.) NaH / 1.) DMF, 50 deg C, 2.5 h, 2.) DMF, 50 deg C, 30 min

2: H₂, NH₃ / Raney Ni / methanol / 3 h / 2585.7 Torr

3: Et₃N / CHCl₃ / 0.5 h / 25 °C

4: 41 percent / 80percent m-chloroperbenzoic acid / CHCl₃ / 16 h / 25 °C

5: 82 percent / Et₃N, Ac₂O / tetrahydrofuran / 20 h / 25 °C

6: 45 percent / conc. HCl / 3 h / Heating

7: conc.H₂SO₄ / 1.) water, reflux, 30 min, 2.) water

8: NaBH₄ / ethanol / 24 h / 25 °C

9: 73 percent / H₂, 12N HCl / Pd/C / H₂O; acetic acid / 0.5 h / 25 °C / 2585.7 Torr

10: 25 percent / BBr₃ / CH₂Cl₂ / a) 25 deg C, 30 min, b) reflux, 1 h

With hydrogenchloride; sodium tetrahydroborate; sulfuric acid; ammonia; hydrogen; acetic anhydride; boron tribromide; sodium hydride; triethylamine; 3-chloro-benzenecarboperoxoic acid; palladium on activated charcoal; nickel; In tetrahydrofuran; methanol; ethanol; dichloromethane; chloroform; water; acetic acid;

DOI:10.1021/jm00150a010

upstream raw materials:

5-<2-<<2-(4-methoxyphenyl)ethyl>amino>ethyl>-8-methoxycarbostyril

3-(4-methoxyphenyl)-oxiranecarbonitrile

2-(8-hydroxyquinolin-5-yl)acetonitrile

4-methoxy-benzaldehyde

Refernces