N-[3,5-dichloro-4-(5-isopropyl-6-methoxy-naphthalen-1-yl)-phenyl]-malonamic acid ethyl ester

Base Information

• Chemical Name: N-[3,5-dichloro-4-(5-isopropyl-6-methoxy-naphthalen-1-yl)-phenyl]-malonamic acid ethyl ester
• CAS No.: 588718-06-3
• Molecular Formula: C₂₅H₂₅Cl₂NO₄
• Molecular Weight: 474.384
• Mol file: 588718-06-3.mol

Synonyms:N-[3,5-dichloro-4-(5-isopropyl-6-methoxy-naphthalen-1-yl)-phenyl]-malonamic acid ethyl ester

Chemical Property of N-[3,5-dichloro-4-(5-isopropyl-6-methoxy-naphthalen-1-yl)-phenyl]-malonamic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-[3,5-dichloro-4-(5-isopropyl-6-methoxy-naphthalen-1-yl)-phenyl]-malonamic acid ethyl ester

There total 10 articles about N-[3,5-dichloro-4-(5-isopropyl-6-methoxy-naphthalen-1-yl)-phenyl]-malonamic 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: 91.0%

3,5-dichloro-4-(5-isopropyl-6-methoxy-naphthalen-1-yl)-phenylamine (588718-05-2) + ethyl chlorocarbonylacetate (36239-09-5) → N-[3,5-dichloro-4-(5-isopropyl-6-methoxy-naphthalen-1-yl)-phenyl]-malonamic acid ethyl ester (588718-06-3)

Guidance literature:

With triethylamine; In dichloromethane; at 0 - 20 ℃; for 2h;

DOI:10.1016/j.bmcl.2005.06.093

Reference yield:

2-(6-methoxynaphthalen-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (588717-94-6) → N-[3,5-dichloro-4-(5-isopropyl-6-methoxy-naphthalen-1-yl)-phenyl]-malonamic acid ethyl ester (588718-06-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 69 percent / aq. Na₂CO₃; Pd(PPh₃)4 / 1,2-dimethoxy-ethane / 0.5 h / 80 °C

2: 77 percent / (CH₃)2SBF₃ / CH₂Cl₂ / 16 h / 20 °C

3: 27 percent / TiCl₄ / CH₂Cl₂; tetrahydrofuran / 16 h / 20 °C

4: 99 percent / aq. acetic acid; iron / 16 h / 20 °C

5: 97 percent / H₂ / PtO₂ / ethanol / 2 h / 760 Torr

6: 91 percent / Et₃N / CH₂Cl₂ / 2 h / 0 - 20 °C

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; boron dimethyl-trifluoro sulphide; hydrogen; titanium tetrachloride; iron; sodium carbonate; acetic acid; triethylamine; platinum(IV) oxide; In tetrahydrofuran; 1,2-dimethoxyethane; ethanol; dichloromethane; 1: Suzuki coupling;

DOI:10.1016/j.bmcl.2005.06.093

Reference yield:

trifluoro-methanesulfonic acid 2,6-dichloro-4-nitrophenyl ester (525584-77-4) → N-[3,5-dichloro-4-(5-isopropyl-6-methoxy-naphthalen-1-yl)-phenyl]-malonamic acid ethyl ester (588718-06-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 69 percent / aq. Na₂CO₃; Pd(PPh₃)4 / 1,2-dimethoxy-ethane / 0.5 h / 80 °C

2: 77 percent / (CH₃)2SBF₃ / CH₂Cl₂ / 16 h / 20 °C

3: 27 percent / TiCl₄ / CH₂Cl₂; tetrahydrofuran / 16 h / 20 °C

4: 99 percent / aq. acetic acid; iron / 16 h / 20 °C

5: 97 percent / H₂ / PtO₂ / ethanol / 2 h / 760 Torr

6: 91 percent / Et₃N / CH₂Cl₂ / 2 h / 0 - 20 °C

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; boron dimethyl-trifluoro sulphide; hydrogen; titanium tetrachloride; iron; sodium carbonate; acetic acid; triethylamine; platinum(IV) oxide; In tetrahydrofuran; 1,2-dimethoxyethane; ethanol; dichloromethane; 1: Suzuki coupling;

DOI:10.1016/j.bmcl.2005.06.093

upstream raw materials:

3,5-dichloro-4-(5-isopropyl-6-methoxy-naphthalen-1-yl)-phenylamine

ethyl chlorocarbonylacetate

2-(6-methoxynaphthalen-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

trifluoro-methanesulfonic acid 2,6-dichloro-4-nitrophenyl ester

Refernces