6-(Benzyloxy)-2-chloroquinoline

Base Information

• Chemical Name: 6-(Benzyloxy)-2-chloroquinoline
• CAS No.: 623144-17-2
• Molecular Formula: C16H12ClNO
• Molecular Weight: 269.73
• DSSTox Substance ID: DTXSID70459182
• Wikidata: Q27121238
• Metabolomics Workbench ID: 57016
• Mol file: 623144-17-2.mol

Synonyms:6-(benzyloxy)-2-chloroquinoline;623144-17-2;2-chloro-6-phenylmethoxyquinoline;SCHEMBL1550777;6-Benzyloxy-2-chloro-quinoline;CHEBI:48488;DTXSID70459182;CYCJPIBUDBOUQD-UHFFFAOYSA-N;AKOS013530521;SB71307;A1-39982;Q27121238

Chemical Property of 6-(Benzyloxy)-2-chloroquinoline

Chemical Property:

• XLogP3: 4.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 269.0607417
• Heavy Atom Count: 19
• Complexity: 280

Purity/Quality:

95+% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=CC=C(C=C1)COC2=CC3=C(C=C2)N=C(C=C3)Cl

Technology Process of 6-(Benzyloxy)-2-chloroquinoline

There total 2 articles about 6-(Benzyloxy)-2-chloroquinoline 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: 94.0%

6-hydroxy-2-chloroquinoline (577967-89-6) + benzyl bromide (100-39-0) → 6-(benzyloxy)-2-chloroquinoline (623144-17-2)

Guidance literature:

With caesium carbonate; In N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2006.09.069

Reference yield:

quinoline-2,6-diol (19315-93-6) → 6-(benzyloxy)-2-chloroquinoline (623144-17-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 98 percent / POCl₃ / dimethylformamide

2: 94 percent / cesium carbonate / dimethylformamide

With caesium carbonate; trichlorophosphate; In N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2006.09.069

Reference yield: 70.0%

6-(benzyloxy)-2-chloroquinoline (623144-17-2) + phenol (108-95-2,27073-41-2) → 6-(benzyloxy)-2-phenoxyquinoline (623144-18-3)

Guidance literature:

phenol; With sodium hydroxide; In water; at 20 ℃; for 0.833333h;

6-(benzyloxy)-2-chloroquinoline; With tetrabutyl-ammonium chloride; In water; toluene; for 24h; Heating / reflux;

upstream raw materials:

6-hydroxy-2-chloroquinoline

benzyl bromide

quinoline-2,6-diol

Downstream raw materials:

6-(benzyloxy)-2-(2,6-dichlorophenyl)quinoline

2-(2,6-dichlorophenyl)-6-quinolinol

2-(2,6-dichlorophenyl)-6-quinolinyl trifluoromethanesulfonate

6-(benzyloxy)-2-phenoxyquinoline

Refernces

• 1、 -. "NOVEL TETRAMETHYL SUBSTITUTED PIPERIDINE DERIVATIVES AND THEIR USE AS MONOAMINE NEUROTRANSMITTER RE-UPTAKE INHIBITORS". Page/Page column 13. . Retrieved 2010/01/30.
• 2、 -. "2,6-QUINOLINYL AND 2,6-NAPHTHYL DERIVATIVES, PROCESSES FOR PREPARING THEM AND THEIR USES AS VLA-4 INHIBITORS". Page/Page column 52. . Retrieved 2010/02/07.