methyl 4'-(2-naphthamido)biphenyl-3-carboxylate

Base Information

• Chemical Name: methyl 4'-(2-naphthamido)biphenyl-3-carboxylate
• CAS No.: 1360630-30-3
• Molecular Formula: C₂₅H₁₉NO₃
• Molecular Weight: 381.431
• Mol file: 1360630-30-3.mol

Synonyms:methyl 4'-(2-naphthamido)biphenyl-3-carboxylate

Chemical Property of methyl 4'-(2-naphthamido)biphenyl-3-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 4'-(2-naphthamido)biphenyl-3-carboxylate

There total 4 articles about methyl 4'-(2-naphthamido)biphenyl-3-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: 29.0%

methyl 4' amino-[1,1'-biphenyl]-3-carboxylate (400747-22-0) + naphthalene-2-carboxylate (93-09-4) → methyl 4'-(2-naphthamido)biphenyl-3-carboxylate (1360630-30-3)

Guidance literature:

naphthalene-2-carboxylate; With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; for 0.25h;

methyl 4' amino-[1,1'-biphenyl]-3-carboxylate; In N,N-dimethyl-formamide; for 48h;

DOI:10.1016/j.bmc.2011.12.040

Reference yield:

4'-nitrobiphenyl-3-carboxylic acid (729-01-1) → methyl 4'-(2-naphthamido)biphenyl-3-carboxylate (1360630-30-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: thionyl chloride / 70 °C

2.1: palladium 10% on activated carbon; hydrogen / methanol / 15 h / 20 °C

3.1: O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.25 h

3.2: 48 h

With thionyl chloride; palladium 10% on activated carbon; hydrogen; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In methanol; N,N-dimethyl-formamide;

DOI:10.1016/j.bmc.2011.12.040

Reference yield:

3-Carboxyphenylboronic acid (25487-66-5) → methyl 4'-(2-naphthamido)biphenyl-3-carboxylate (1360630-30-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate / ethanol; water; toluene / 48 h / Inert atmosphere; Reflux

1.2: pH 3

2.1: thionyl chloride / 70 °C

3.1: palladium 10% on activated carbon; hydrogen / methanol / 15 h / 20 °C

4.1: O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.25 h

4.2: 48 h

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; thionyl chloride; palladium 10% on activated carbon; hydrogen; potassium carbonate; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In methanol; ethanol; water; N,N-dimethyl-formamide; toluene; 1.1: Suzuki coupling;

DOI:10.1016/j.bmc.2011.12.040

upstream raw materials:

methyl 4' amino-[1,1'-biphenyl]-3-carboxylate

naphthalene-2-carboxylate

4'-nitrobiphenyl-3-carboxylic acid

3-Carboxyphenylboronic acid