4-[(2,2-DiMethyl-4,6-dioxo-[1,3]dioxan-5-ylideneMethyl)-aMino]-benzoic acid ethyl ester

Base Information

• Chemical Name: 4-[(2,2-DiMethyl-4,6-dioxo-[1,3]dioxan-5-ylideneMethyl)-aMino]-benzoic acid ethyl ester
• CAS No.: 205810-04-4
• Molecular Formula: C16H17NO6
• Molecular Weight: 319.30928
• Mol file: 205810-04-4.mol

Synonyms:4-[(2,2-DiMethyl-4,6-dioxo-[1,3]dioxan-5-ylideneMethyl)-aMino]-benzoic acid ethyl ester

Chemical Property of 4-[(2,2-DiMethyl-4,6-dioxo-[1,3]dioxan-5-ylideneMethyl)-aMino]-benzoic acid ethyl ester

Chemical Property:

• PSA: 90.93000
• LogP: 2.06820
• Storage Temp.: 2-8°C

Purity/Quality:

97% ^*data from raw suppliers

4-[(2,2-Dimethyl-4,6-dioxo-[1,3]dioxan-5-ylidenemethyl)-amino]benzoicAcidEthylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 4-[(2,2-DiMethyl-4,6-dioxo-[1,3]dioxan-5-ylideneMethyl)-aMino]-benzoic acid ethyl ester

There total 1 articles about 4-[(2,2-DiMethyl-4,6-dioxo-[1,3]dioxan-5-ylideneMethyl)-aMino]-benzoic acid ethyl ester 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: 88.0%

cycl-isopropylidene malonate (2033-24-1) + p-aminoethylbenzoate (94-09-7) + trimethyl orthoformate (149-73-5) → ethyl 4-(((2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ylidene)methyl)amino)benzoate (205810-04-4)

Guidance literature:

cycl-isopropylidene malonate; trimethyl orthoformate; at 110 ℃; for 1h; Inert atmosphere;

p-aminoethylbenzoate; at 110 ℃; for 6h; Inert atmosphere;

DOI:10.1002/anie.201507849

Reference yield: 89.0%

ethyl 4-(((2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ylidene)methyl)amino)benzoate (205810-04-4) → ethyl 4-oxo-1,4-dihydroquinoline-6-carboxylate (127286-04-8,148018-33-1)

Guidance literature:

In diphenylether; at 180 - 210 ℃; for 0.166667 - 0.25h;

Reference yield:

ethyl 4-(((2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ylidene)methyl)amino)benzoate (205810-04-4) → diethyl (3aR,4R,9bS)-1-benzyl-4-(3-(benzyl((benzyloxy)carbonyl)amino)prop-1-yn-1-yl)-1,2,3,3a,4,9b-hexahydro-5H-pyrrolo[3,2-c]quinoline-5,8-dicarboxylate

Guidance literature:

Multi-step reaction with 6 steps

1.1: diphenylether / 1 h / Inert atmosphere

2.1: dichloromethane / 0.08 h / -10 °C / Inert atmosphere

2.2: 18 h / -10 °C / Inert atmosphere

3.1: dichloromethane / 0.08 h / 20 °C / Inert atmosphere

3.2: 42 h / -25 °C / Inert atmosphere

4.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / tetrahydrofuran / 3 h / 20 °C / Inert atmosphere; Glovebox

5.1: ozone / dichloromethane / 0.17 h / -78 °C / Inert atmosphere

5.2: 18 h / -78 - 20 °C / Inert atmosphere

6.1: sodium cyanoborohydride / methanol / 19.5 h / 20 °C / Inert atmosphere

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium cyanoborohydride; ozone; In tetrahydrofuran; methanol; diphenylether; dichloromethane;

DOI:10.1002/anie.201507849

upstream raw materials:

cycl-isopropylidene malonate

p-aminoethylbenzoate

trimethyl orthoformate

Downstream raw materials:

ethyl 4-oxo-1,4-dihydroquinoline-6-carboxylate

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