6-amino-naphthalene-1-carboxylic acid methyl ester

Base Information

• Chemical Name: 6-amino-naphthalene-1-carboxylic acid methyl ester
• CAS No.: 91569-20-9
• Molecular Formula: C₁₂H₁₁NO₂
• Molecular Weight: 201.225
• Mol file: 91569-20-9.mol

Synonyms:1-Naphthoicacid, 6-amino-, methyl ester (7CI); Methyl 6-amino-1-naphthoate

Chemical Property of 6-amino-naphthalene-1-carboxylic acid methyl ester

Chemical Property:

• PSA: 52.32000
• LogP: 2.78980

Purity/Quality:

99%,98% ^*data from raw suppliers

Methyl2-aminonaphthalene-5-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 6-amino-naphthalene-1-carboxylic acid methyl ester

There total 4 articles about 6-amino-naphthalene-1-carboxylic acid methyl 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: 95.0%

6-trifluoromethanesulfonyloxy-naphthalene-1-carboxylic acid methyl ester (255050-65-8) → methyl 6-amino-1-naphthalenecarboxylate (91569-20-9)

Guidance literature:

With Benzophenone imine; potassium phosphate; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; In 1,2-dimethoxyethane; at 90 ℃; for 8h;

DOI:10.1021/jm701097z

Reference yield:

methyl 6-hydroxy-1-naphthoate (90162-13-3) → methyl 6-amino-1-naphthalenecarboxylate (91569-20-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / -78 °C

2.1: Benzophenone imine; CyJohnPhos; potassium phosphate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾ / 1,2-dimethoxyethane / 3 h / 90 °C / Inert atmosphere

2.2: 0.5 h / 20 °C / Inert atmosphere

2.3: pH 10 / Inert atmosphere

With Benzophenone imine; potassium phosphate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; N-ethyl-N,N-diisopropylamine; CyJohnPhos; In 1,2-dimethoxyethane; dichloromethane; 2.1: |Buchwald-Hartwig Coupling / 2.2: |Buchwald-Hartwig Coupling;

DOI:10.1039/c5md00191a

Reference yield:

6-hydroxy-1-naphthoic acid (2437-17-4) → methyl 6-amino-1-naphthalenecarboxylate (91569-20-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: thionyl chloride / 2 h / Reflux

2.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / -78 °C

3.1: Benzophenone imine; CyJohnPhos; potassium phosphate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾ / 1,2-dimethoxyethane / 3 h / 90 °C / Inert atmosphere

3.2: 0.5 h / 20 °C / Inert atmosphere

3.3: pH 10 / Inert atmosphere

With Benzophenone imine; potassium phosphate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; thionyl chloride; N-ethyl-N,N-diisopropylamine; CyJohnPhos; In 1,2-dimethoxyethane; dichloromethane; 3.1: |Buchwald-Hartwig Coupling / 3.2: |Buchwald-Hartwig Coupling;

DOI:10.1039/c5md00191a

upstream raw materials:

6-trifluoromethanesulfonyloxy-naphthalene-1-carboxylic acid methyl ester

methyl 6-hydroxy-1-naphthoate

6-hydroxy-1-naphthoic acid

Refernces

• 1、 Lv, Yongcong,Li, Mengyuan,Cao, Sufen,Tong, Linjiang,Peng, Ting,Wei, Lixin,Xie, Hua,Ding, Jian,Duan, Wenhu. "Discovery of anilinopyrimidine-based naphthamide derivatives as potent VEGFR-2 inhibitors". supporting information. p. 1375 - 1380. Retrieved 2015/07/15.