methyl 6-bromo-7-(4-methoxyphenyl)amino-1,3-dimethyl-5,8-dioxo-5,8-dihydroisoquinoline-4-carboxylate

Base Information

• Chemical Name: methyl 6-bromo-7-(4-methoxyphenyl)amino-1,3-dimethyl-5,8-dioxo-5,8-dihydroisoquinoline-4-carboxylate
• CAS No.: 1428248-10-5
• Molecular Formula: C₂₀H₁₇BrN₂O₅
• Molecular Weight: 445.269
• Mol file: 1428248-10-5.mol

Synonyms:methyl 6-bromo-7-(4-methoxyphenyl)amino-1,3-dimethyl-5,8-dioxo-5,8-dihydroisoquinoline-4-carboxylate

Chemical Property of methyl 6-bromo-7-(4-methoxyphenyl)amino-1,3-dimethyl-5,8-dioxo-5,8-dihydroisoquinoline-4-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 6-bromo-7-(4-methoxyphenyl)amino-1,3-dimethyl-5,8-dioxo-5,8-dihydroisoquinoline-4-carboxylate

There total 6 articles about methyl 6-bromo-7-(4-methoxyphenyl)amino-1,3-dimethyl-5,8-dioxo-5,8-dihydroisoquinoline-4-carboxylate 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: 83.0%

methyl 6,7-dibromo-5,8-dihydro-1,3-dimethyl-5,8-dioxoisoquinoline-4-carboxylate (1428248-22-9) + 4-methoxy-aniline (104-94-9) → methyl 6-bromo-7-(4-methoxyphenyl)amino-1,3-dimethyl-5,8-dioxo-5,8-dihydroisoquinoline-4-carboxylate (1428248-10-5)

Guidance literature:

In ethanol; at 50 ℃; for 0.5h; regioselective reaction;

DOI:10.1016/j.bmcl.2013.01.130

Reference yield: 60.0%

1,3-dimethyl-5,8-dioxo-5,8-dihydroisoquinoline-4-carboxylic acid methyl ester (900189-14-2) + 4-methoxy-aniline (104-94-9) → methyl 6-bromo-7-(4-methoxyphenyl)amino-1,3-dimethyl-5,8-dioxo-5,8-dihydroisoquinoline-4-carboxylate (1428248-10-5) + methyl 6-bromo-3-bromomethyl-7-(4-methoxyphenyl)amino-1-methyl-5,8-dioxo-5,8-dihydroisoquinoline-4-carboxylate

Guidance literature:

1,3-dimethyl-5,8-dioxo-5,8-dihydroisoquinoline-4-carboxylic acid methyl ester; With sodium acetate; acetic acid; at 20 ℃; for 0.166667h;

With bromine; at 20 ℃; for 1h; Sonication;

4-methoxy-aniline; In ethanol; at 20 ℃; for 1h;

DOI:10.1039/c7ra00825b

Reference yield:

2,5-Dihydroxyacetophenone (490-78-8) → methyl 6-bromo-7-(4-methoxyphenyl)amino-1,3-dimethyl-5,8-dioxo-5,8-dihydroisoquinoline-4-carboxylate (1428248-10-5) + methyl 6-bromo-3-bromomethyl-7-(4-methoxyphenyl)amino-1-methyl-5,8-dioxo-5,8-dihydroisoquinoline-4-carboxylate

Guidance literature:

Multi-step reaction with 2 steps

1.1: manganese(IV) oxide; magnesium sulfate / dichloromethane

2.1: sodium acetate; acetic acid / 0.17 h / 20 °C

2.2: 1 h / 20 °C / Sonication

2.3: 1 h / 20 °C

With manganese(IV) oxide; sodium acetate; magnesium sulfate; acetic acid; In dichloromethane;

DOI:10.1039/c7ra00825b

upstream raw materials:

2,5-Dihydroxyacetophenone

1,3-dimethyl-5,8-dioxo-5,8-dihydroisoquinoline-4-carboxylic acid methyl ester

methyl 6,7-dibromo-5,8-dihydro-1,3-dimethyl-5,8-dioxoisoquinoline-4-carboxylate

4-methoxy-aniline