1-(2-methoxy-4-methoxycarbonylbenzyl)-5-nitro-4-oxo-1,4-dihydroquinoline

Base Information

• Chemical Name: 1-(2-methoxy-4-methoxycarbonylbenzyl)-5-nitro-4-oxo-1,4-dihydroquinoline
• CAS No.: 188244-54-4
• Molecular Formula: C₁₉H₁₆N₂O₆
• Molecular Weight: 368.346
• Mol file: 188244-54-4.mol

Synonyms:1-(2-methoxy-4-methoxycarbonylbenzyl)-5-nitro-4-oxo-1,4-dihydroquinoline

Chemical Property of 1-(2-methoxy-4-methoxycarbonylbenzyl)-5-nitro-4-oxo-1,4-dihydroquinoline

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-(2-methoxy-4-methoxycarbonylbenzyl)-5-nitro-4-oxo-1,4-dihydroquinoline

There total 2 articles about 1-(2-methoxy-4-methoxycarbonylbenzyl)-5-nitro-4-oxo-1,4-dihydroquinoline 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:

methyl 4-methyl-3-methoxybenzoate (3556-83-0) → 1-(2-methoxy-4-methoxycarbonylbenzyl)-5-nitro-4-oxo-1,4-dihydroquinoline (188244-54-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 97 percent / NBS, AIBN / CCl₄ / 4 h / Heating

2: 2.) NaH / 1.) diphenyl ether, reflux, 20 min, 2.) THF, 0 deg C, 30 min, 3.) reflux, 4 h

With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); sodium hydride; In tetrachloromethane;

DOI:10.1016/S0223-5234(97)83282-5

Reference yield:

methyl 4-(bromomethyl)-3-methoxybenzoate (70264-94-7) + 2,2-dimethyl-5-((3-nitrophenylamino)methylene)-1,3-dioxane-4,6-dione (25063-48-3) → 1-(2-methoxy-4-methoxycarbonylbenzyl)-5-nitro-4-oxo-1,4-dihydroquinoline (188244-54-4) + 1-(2-methoxy-4-methoxycarbonylbenzyl)-7-nitro-4-oxo-1,4-dihydroquinoline (188244-56-6)

Guidance literature:

With sodium hydride; Yield given. Multistep reaction. Yields of byproduct given; 1.) diphenyl ether, reflux, 20 min, 2.) THF, 0 deg C, 30 min, 3.) reflux, 4 h;

DOI:10.1016/S0223-5234(97)83282-5

Reference yield: 98.0%

1-(2-methoxy-4-methoxycarbonylbenzyl)-5-nitro-4-oxo-1,4-dihydroquinoline (188244-54-4) → 5-amino-1-(2-methoxy-4-methoxycarbonylbenzyl)-4-oxo-1,4-dihydroquinoline (188244-57-7)

Guidance literature:

With ammonium formate; palladium on activated charcoal; In methanol; for 2.5h; Heating;

DOI:10.1016/S0223-5234(97)83282-5

upstream raw materials:

methyl 4-(bromomethyl)-3-methoxybenzoate

2,2-dimethyl-5-((3-nitrophenylamino)methylene)-1,3-dioxane-4,6-dione

methyl 4-methyl-3-methoxybenzoate

Downstream raw materials:

5-amino-1-(2-methoxy-4-methoxycarbonylbenzyl)-4-oxo-1,4-dihydroquinoline

4-[5-(2-Cyclopentyl-acetylamino)-4-oxo-4H-quinolin-1-ylmethyl]-3-methoxy-benzoic acid

4-[5-(2-Cyclopentyl-acetylamino)-4-oxo-4H-quinolin-1-ylmethyl]-3-methoxy-benzoic acid methyl ester

Refernces