8-Benzyloxy-5-(2-bromoacetyl)-2-hydroxyquinoline

Base Information

• Chemical Name: 8-Benzyloxy-5-(2-bromoacetyl)-2-hydroxyquinoline
• CAS No.: 100331-89-3
• Molecular Formula: C18H14BrNO3
• Molecular Weight: 372.218
• Hs Code.: 2942000000
• European Community (EC) Number: 675-817-4
• DSSTox Substance ID: DTXSID50470330
• Nikkaji Number: J2.538.210B
• Wikidata: Q72441801
• Mol file: 100331-89-3.mol

Synonyms:100331-89-3;8-Benzyloxy-5-(2-bromoacetyl)-2-hydroxyquinoline;1-(8-(benzyloxy)-2-hydroxyquinolin-5-yl)-2-bromoethanone;8-(Benzyloxy)-5-(2-bromoacetyl)quinolin-2(1H)-one;8-benzyloxy-5-(2-bromo-acetyl)-1h-quinolin-2-one;5-(2-bromoacetyl)-8-phenylmethoxy-1H-quinolin-2-one;MFCD09025318;8-Benzyloxy-5-(2-Bromoacetyl)-1H-quinolin-2-one;8-Benzyloxy-5-(2-bromoacetyl)-2(1H)-quinolinone;8-Benzyloxy-5-bromoacetylcarbostyril;5-Bromoacetyl-8-benzyloxycarbostyril;2(1H)-Quinolinone, 5-(bromoacetyl)-8-(phenylmethoxy)-;SCHEMBL99439;8-(Benzyloxy)-5-(bromoacetyl)quinolin-2(1H)-one;DTXSID50470330;RVHSDLUBNZBRMH-UHFFFAOYSA-N;1-[8-(benzyloxy)-2-hydroxyquinolin-5-yl]-2-bromoethan-1-one;BCP22356;AKOS015920361;AKOS025214116;SB73046;AC-24608;SY045270;CS-0100873;FT-0630054;A16169;8-benzyloxy-5-(2-bromoacetyl)quinolin-2(1h)-one;8-Benzyloxy 5-(2-bromoacetyl)-1H-quinolin-2-one;J-000105;J-519371

Chemical Property of 8-Benzyloxy-5-(2-bromoacetyl)-2-hydroxyquinoline

Chemical Property:

• Appearance/Colour: Off-white solid
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.638
• Boiling Point: 602.645 °C at 760 mmHg
• PKA: 10.38±0.70(Predicted)
• Flash Point: 318.268 °C
• PSA: 59.42000
• Density: 1.48 g/cm³
• LogP: 4.09700
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility.: Chloroform (Sparingly), Ethyl Acetate (Slightly)
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 371.01571
• Heavy Atom Count: 23
• Complexity: 473

Purity/Quality:

99%min ^*data from raw suppliers

8-Benzyloxy-5-(2-bromoacetyl)-2(1H)-quinolinone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)COC2=C3C(=C(C=C2)C(=O)CBr)C=CC(=O)N3
• Uses: 8-(benzyloxy)-5-(2-broMoacetyl)quinolin-2(1H)-one can be used in the preparation of phenylethanolamine derivatives as β2 adrenoreceptor agonists.

Technology Process of 8-Benzyloxy-5-(2-bromoacetyl)-2-hydroxyquinoline

There total 13 articles about 8-Benzyloxy-5-(2-bromoacetyl)-2-hydroxyquinoline 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: 82.9%

5-acetyl-8-benzyloxy-1H-quinolin-2-one (93609-84-8) → 8-benzyloxy-5-(2-bromoacetyl)-1H-quinolin-2-one (100331-89-3)

Guidance literature:

With aluminum (III) chloride; bromine; In dichloromethane; at 0 - 20 ℃; for 4.5h;

Reference yield: 73.0%

tetra-n-butylammonium tribromide + 5-acetyl-8-benzyloxy-1H-quinolin-2-one (93609-84-8) → 8-benzyloxy-5-(2-bromoacetyl)-1H-quinolin-2-one (100331-89-3)

Guidance literature:

In tetrahydrofuran; methanol;

Reference yield:

5-acetyl-8-hydroxy-2(1H)-quinolinone (62978-73-8) → 8-benzyloxy-5-(2-bromoacetyl)-1H-quinolin-2-one (100331-89-3)

Guidance literature:

Multi-step reaction with 2 steps

1: potassium carbonate / N,N-dimethyl-formamide / 2 h / 20 °C

2: pyridinium hydrobromide perbromide / tetrahydrofuran / 0 °C / Reflux

With pyridinium hydrobromide perbromide; potassium carbonate; In tetrahydrofuran; N,N-dimethyl-formamide;

upstream raw materials:

5-acetyl-8-benzyloxy-1H-quinolin-2-one

8-Hydroxyquinoline-N-oxide

8-quinolinol

2-oxo-1,2-dihydroquinolin-8-yl acetate

Downstream raw materials:

8-(benzyloxy)-5-(2-bromo-1-hydroxyethyl)quinolin-2(1H)-one

8-(benzyloxy)-5-[(1R)-2-bromo-1-hydroxyethyl]quinolin-2(1H)-one

5-[[[(1R)-2-(4-methoxyphenyl)-1-methylethyl](phenylmethyl)amino]acetyl]-8-(phenylmethoxy)-(1H)-quinolin-2-one monohydrochloride

2-(4-((((R)-2-Hydroxy-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethyl)amino)methyl)-2-methylphenoxy)ethyl 4-((3-((S)-phenyl((((R)-quinuclidin-3-yloxy)carbonyl)amino)methyl)phenoxy)methyl)benzoate

Refernces

• 1、 -. "CLASS OF BIFUNCTIONAL COMPOUNDS WITH QUATERNARY AMMONIUM SALT STRUCTURE". Paragraph 0159. . Retrieved 2019/11/11.
• 2、 -. "A Process for Preparing Indacaterol and Salts Thereof". Paragraph 0070. . Retrieved 2018/08/20.