4-(Benzyloxy)-2-(chloromethyl)-3-methylquinoline

Base Information

• Chemical Name: 4-(Benzyloxy)-2-(chloromethyl)-3-methylquinoline
• CAS No.: 356761-10-9
• Molecular Formula: C18H16ClNO
• Molecular Weight: 297.78
• Hs Code.: 2933499090
• DSSTox Substance ID: DTXSID80445516
• Wikidata: Q82263955
• Mol file: 356761-10-9.mol

Synonyms:4-(Benzyloxy)-2-(chloromethyl)-3-methylquinoline;356761-10-9;4-Benzyloxy-2-chloromethyl-3-methyl-quinoline;2-(chloromethyl)-3-methyl-4-phenylmethoxyquinoline;4-BENZYLOXY-2-CHLOROMETHYL-3-METHYLQUINOLINE;C18H16ClNO;SCHEMBL3092020;DTXSID80445516;PTNAVHVIDBXIJY-UHFFFAOYSA-N;AB65708;A848394

Chemical Property of 4-(Benzyloxy)-2-(chloromethyl)-3-methylquinoline

Chemical Property:

• PSA: 22.12000
• LogP: 4.86100
• XLogP3: 4.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 297.0920418
• Heavy Atom Count: 21
• Complexity: 318

Purity/Quality:

97% ^*data from raw suppliers

4-(Benzyloxy)-2-(chloromethyl)-3-methylquinoline 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C2=CC=CC=C2N=C1CCl)OCC3=CC=CC=C3

Technology Process of 4-(Benzyloxy)-2-(chloromethyl)-3-methylquinoline

There total 9 articles about 4-(Benzyloxy)-2-(chloromethyl)-3-methylquinoline 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: 75.0%

4-(benzyloxy)-2,3-dimethylquinoline 1-oxide (275356-90-6) → 4-(benzyloxy)-2-(chloromethyl)-3-methylquinoline (356761-10-9)

Guidance literature:

With p-toluenesulfonyl chloride; In acetonitrile; at 20 ℃; for 48h;

DOI:10.1039/d0cc02498h

Reference yield: 75.0%

p-toluenesulfonyl chloride (98-59-9) + 4-(benzyloxy)-2,3-dimethylquinoline 1-oxide (275356-90-6) → 4-(benzyloxy)-2-(chloromethyl)-3-methylquinoline (356761-10-9)

Guidance literature:

p-toluenesulfonyl chloride; 4-(benzyloxy)-2,3-dimethylquinoline 1-oxide; With potassium carbonate; In acetonitrile; at 20 ℃;

With potassium carbonate; p-toluenesulfonyl chloride; In acetonitrile; at 20 ℃;

DOI:10.7164/antibiotics.53.418

Reference yield:

4-(benzyloxy)-2,3-dimethylquinoline (275356-89-3) → 4-(benzyloxy)-2-(chloromethyl)-3-methylquinoline (356761-10-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 85 percent / m-chloroperoxybenzoic acid (MCPBA) / CHCl₃ / 20 °C

2.1: K₂CO₃ / acetonitrile / 20 °C

2.2: 75 percent / K₂CO₃; TsCl / acetonitrile / 20 °C

With potassium carbonate; 3-chloro-benzenecarboperoxoic acid; In chloroform; acetonitrile; 1.1: Oxidation / 2.1: Substitution / 2.2: Chlorination;

DOI:10.7164/antibiotics.53.418

upstream raw materials:

p-toluenesulfonyl chloride

4-(benzyloxy)-2,3-dimethylquinoline 1-oxide

2-acetylpropanoic acid ethyl ester

benzyl chloride

Downstream raw materials:

(4E)-5-[4-(benzyloxy)-3-methylquinolin-2-yl]penten-1-ol

3-[4-(benzyloxy)-3-methylquinolin-2-yl]-N-(3-phenylpropyl)propanamide

3-[4-(benzyloxy)-3-methylquinolin-2-yl]propionic acid

C₂₇H₃₃NO₄