DIETHYL 2-(((2,5-DIMETHOXYPHENYL)AMINO)METHYLENE)PROPANE-1,3-DIOATE

Base Information

• Chemical Name: DIETHYL 2-(((2,5-DIMETHOXYPHENYL)AMINO)METHYLENE)PROPANE-1,3-DIOATE
• CAS No.: 26833-01-2
• Molecular Formula: C16H21NO6
• Molecular Weight: 323.34100
• Mol file: 26833-01-2.mol

Synonyms:DIETHYL-2-[(2,5-DIMETHOXYANILINO)METHYLENE]MALONATE;N-(2,2-dicarbetoxyethenyl)-2,5-dimethoxyaniline;(2,5-Dimethoxy-anilinomethylen)-malonsaeurediaethylester;

Chemical Property of DIETHYL 2-(((2,5-DIMETHOXYPHENYL)AMINO)METHYLENE)PROPANE-1,3-DIOATE

Chemical Property:

• PSA: 83.09000
• LogP: 2.19880

Purity/Quality:

DIETHYL-2-[(2,5-DIMETHOXYANILINO)METHYLENE]MALONATE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of DIETHYL 2-(((2,5-DIMETHOXYPHENYL)AMINO)METHYLENE)PROPANE-1,3-DIOATE

There total 1 articles about DIETHYL 2-(((2,5-DIMETHOXYPHENYL)AMINO)METHYLENE)PROPANE-1,3-DIOATE 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: 86.2%

diethyl 2-ethoxymethylenemalonate (87-13-8) + 2,5-dimethoxyaniline (102-56-7,102526-87-4) → N-(2',5'-Dimethoxyphenyl)aminomethylidenmalonsaeure-diaethylester (26833-01-2)

Guidance literature:

In 1,4-dioxane; at 50 ℃; for 20h;

DOI:10.1002/hlca.19820650835

Reference yield: 71.0%

N-(2',5'-Dimethoxyphenyl)aminomethylidenmalonsaeure-diaethylester (26833-01-2) → 4-Hydroxy-5,8-dimethoxy-3-chinolincarbonsaeure-aethylester (5428-19-3)

Guidance literature:

In diphenylether; for 0.25h; Heating;

Reference yield:

N-(2',5'-Dimethoxyphenyl)aminomethylidenmalonsaeure-diaethylester (26833-01-2) → 1-Aethyl-6-(4-nitroanilino)-4,5,8-trioxo-1,4,5,8-tetrahydro-3-chinolincarbonsaeure (85525-82-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 51.7 percent / Dowtherm A / 0.5 h / Heating

2: 1.) NaH / 1.) DMF, 50 deg C, 2 h; 2.) DMF, 50 deg C, 22 h

3: 85.9 percent / KOH, H₂O / 16 h / Ambient temperature

4: 86 percent / cerium(IV)ammonium nitrate / acetonitrile; H₂O / 0.5 h / 0 °C

5: 60 percent / methanol; acetic acid / 20 h

With potassium hydroxide; diphenyl ether-biphenyl eutectic; ammonium cerium(IV) nitrate; water; sodium hydride; In methanol; water; acetic acid; acetonitrile;

DOI:10.1002/hlca.19820650835

upstream raw materials:

diethyl 2-ethoxymethylenemalonate

2,5-dimethoxyaniline

Downstream raw materials:

4-Hydroxy-5,8-dimethoxy-3-chinolincarbonsaeure-aethylester

N-Aethyl-N-(2',5'-dimethoxyphenyl)aminomethylidenmalonsaeure-diaethylester

1-Aethyl-6-(4-nitroanilino)-4,5,8-trioxo-1,4,5,8-tetrahydro-3-chinolincarbonsaeure

1-Aethyl-4,5,8-trioxo-6-(3,4,5-trimethoxyanilino)-1,4,5,8-tetrahydro-3-chinolincarbonsaeure

Refernces

• 1、 Link, Helmut,Bernauer, Karl,Englert, Gerhard. "Abkoemmlinge der 3-Chinolincarbonsaeure mit Sauerstoffsubstitution in Stellung 4,5 und 8: Synthese, Reaktionen, NMR-Studien". . p. 2645 - 2667. Retrieved 2007/10/02.