6-bromo-5-<(methoxycarbonyl)methyl>-6,7-dihydro-1H,5H-pyrido<1,2,3-de>quinoxaline-2,3-dione

Base Information

• Chemical Name: 6-bromo-5-<(methoxycarbonyl)methyl>-6,7-dihydro-1H,5H-pyrido<1,2,3-de>quinoxaline-2,3-dione
• CAS No.: 150533-87-2
• Molecular Formula: C₁₄H₁₃BrN₂O₄
• Molecular Weight: 353.172
• Mol file: 150533-87-2.mol

Synonyms:6-bromo-5-<(methoxycarbonyl)methyl>-6,7-dihydro-1H,5H-pyrido<1,2,3-de>quinoxaline-2,3-dione

Chemical Property of 6-bromo-5-<(methoxycarbonyl)methyl>-6,7-dihydro-1H,5H-pyrido<1,2,3-de>quinoxaline-2,3-dione

Chemical Property:

Purity/Quality:

98%,99%, ^*data from raw suppliers

Methyl 2-(9-bromo-2,3-dioxo-2,3,6,7-tetrahydro-1H,5H-pyrido[1,2,3-de]quinoxalin-5-yl)acetate ≥90% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: This product is Informer compound X1 of the Aryl Halide Chemistry Informer Library developed by chemists at Merck & Co., Inc., Kenilworth, NJ, U.S., which contains 18 drug-like molecules representative of those encountered in complex synthesis. By screening a new reaction against the Informer Library, chemists can directly compare and analyse a reaction′s successes and shortcomings among different methods and various research teams. It may also be used to facilitate deeper method development for performance or utility.

Technology Process of 6-bromo-5-<(methoxycarbonyl)methyl>-6,7-dihydro-1H,5H-pyrido<1,2,3-de>quinoxaline-2,3-dione

There total 14 articles about 6-bromo-5-<(methoxycarbonyl)methyl>-6,7-dihydro-1H,5H-pyrido<1,2,3-de>quinoxaline-2,3-dione 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: 89.0%

6-bromo-2-<(methoxycarbonyl)methyl>-8-nitro-N-ethoxalyltetrahydroquinoline (150535-18-5) → 6-bromo-5-<(methoxycarbonyl)methyl>-6,7-dihydro-1H,5H-pyrido<1,2,3-de>quinoxaline-2,3-dione (150533-87-2)

Guidance literature:

With titanium(III) chloride; In acetone; Ambient temperature;

DOI:10.1021/jm00049a015

Reference yield: 49.0%

aqueous titanium trichloride + 6-bromo-2-<(methoxycarbonyl)methyl>-8-nitro-N-ethoxalyltetrahydroquinoline (150535-18-5) → 6-bromo-5-<(methoxycarbonyl)methyl>-6,7-dihydro-1H,5H-pyrido<1,2,3-de>quinoxaline-2,3-dione (150533-87-2)

Guidance literature:

In hexane; water; acetone; toluene;

Reference yield:

6-bromo-2-<(methoxycarbonyl)methyl>tetrahydroquinoline (150535-16-3) → 6-bromo-5-<(methoxycarbonyl)methyl>-6,7-dihydro-1H,5H-pyrido<1,2,3-de>quinoxaline-2,3-dione (150533-87-2)

Guidance literature:

Multi-step reaction with 3 steps

1: Et₃N / CH₂Cl₂

2: NO₂⁺BF₄^- / CH₂Cl₂

3: TiCl₃, H₂O / acetone

With titanium(III) chloride; nitronium tetrafluoborate; water; triethylamine; In dichloromethane; acetone;

DOI:10.1016/S0957-4166(98)00484-4

upstream raw materials:

6-bromo-2-<(methoxycarbonyl)methyl>-8-nitro-N-ethoxalyltetrahydroquinoline

quinoline-2-carboxylic acid

1,2,3,4-tetrahydroquinolin-2-ylmethanol

1,2,3,4-tetrahydroquinoline-2-carboxylic acid

Downstream raw materials:

9-bromo-5-[(p-aminomethylphenyl)carbamoylmethyl]-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione hydrochloride

9-bromo-5-(p-tert-butoxycarbonylaminomethylphenyl-carbamoylmethyl)-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione

9-bromo-5-(p-methoxycarbonyl-m-chlorophenylcarbamoylmethyl)-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione

9-bromo-5-{[p-2-carboxy-(E)-ethenylphenyl]carbamoylmethyl}-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione

Refernces

• 1、 -. "Tricyclic quinoxalinediones". . . Retrieved 2008/06/13.