2,6-DIMETHOXY-4-METHYLQUINOLINE

Base Information

• Chemical Name: 2,6-DIMETHOXY-4-METHYLQUINOLINE
• CAS No.: 6340-55-2
• Molecular Formula: C11H10 Cl N O
• Molecular Weight: 207.659
• Hs Code.: 2933499090
• Mol file: 6340-55-2.mol

Synonyms:Lepidine,2-chloro-6-methoxy- (6CI,8CI); 2-Chloro-4-methyl-6-methoxyquinoline;2-Chloro-6-methoxy-4-methylquinoline; NSC 13577; NSC 51245

Chemical Property of 2,6-DIMETHOXY-4-METHYLQUINOLINE

Chemical Property:

• PSA: 22.12000
• Density: 1.287g/cm³
• LogP: 3.20520

Purity/Quality:

99%, ^*data from raw suppliers

2-Chloro-6-methoxy-4-methylquinoline ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 2-Chloro-6-methoxy-4-methylquinoline is an intermediate in the synthesis of Tafenoquine-d3 Succinate which is the labelled analog of Tatenoquine (T004760), a new 8-aminoquinoline with an improved therapeutic index and safety profile as compared to primaquine (P733500).Tafenoquine has the potential to become a widely used drug in the prevention and treatment of malaria infection and could replace some currently used drugs as resistant strains of Plasmodium species increase.

Technology Process of 2,6-DIMETHOXY-4-METHYLQUINOLINE

There total 5 articles about 2,6-DIMETHOXY-4-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: 89.3%

2-hydroxy-4-methyl-6-methoxyquinoline (5342-23-4) → 2-chloro-4-methyl-6-methoxyquinoline (6340-55-2)

Guidance literature:

With trichlorophosphate; at 110 - 120 ℃; for 0.5h;

DOI:10.1016/S0960-894X(01)00229-3

Reference yield: 72.0%

→ 2-chloro-4-methyl-6-methoxyquinoline (6340-55-2)

Guidance literature:

With trichlorophosphate; at 80 ℃; for 3h;

Reference yield:

4'-methoxyacetoacetanilide (5437-98-9) → 2-chloro-4-methyl-6-methoxyquinoline (6340-55-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 62.4 percent / H₂SO₄ / 2 h / 90 - 110 °C

2: 89.3 percent / POCl₃ / 0.5 h / 110 - 120 °C

With sulfuric acid; trichlorophosphate;

DOI:10.1016/S0960-894X(01)00229-3

upstream raw materials:

2-hydroxy-4-methyl-6-methoxyquinoline

4'-methoxyacetoacetanilide

4-methoxy-aniline

6-methoxy-4-methyl-2-oxo-1H-quinoline

Downstream raw materials:

4-(6-methoxy-4-methyl-quinolin-2-ylamino)-benzenesulfonamide

6-methoxy-4-methyl-quinoline-2-thiol

2-phenoxy-4-methyl-6-methoxyquinoline

2-(3',5'-dimethylpyrazol-1'-yl)-4-methyl-6-methoxyquinoline

Refernces

• 1、 -. "Process for the preparation of anti-malarial drugs". . . Retrieved 2008/06/13.
• 2、 -. "Pyridine and related aza heterocycle derivatives as cardiovascular agents". . . Retrieved 2008/06/13.