Methyl 4-amino-1-naphthoate

Base Information

• Chemical Name: Methyl 4-amino-1-naphthoate
• CAS No.: 157252-24-9
• Molecular Formula: C₁₂H₁₁NO₂
• Molecular Weight: 201.225
• European Community (EC) Number: 818-756-2
• Nikkaji Number: J832.578B
• Mol file: 157252-24-9.mol

Synonyms:methyl 4-amino-1-naphthoate;157252-24-9;METHYL 4-AMINONAPHTHALENE-1-CARBOXYLATE;1-Naphthalenecarboxylicacid,4-amino-,methylester(9CI);4-Amino-1-naphthalenecarboxylic acid methyl ester;methyl4-amino-1-naphthoate;1-Naphthalenecarboxylic acid, 4-amino-, methyl ester;SCHEMBL4685498;1-AMINONAPHTHALENE-4-CARBOXYLIC ACID METHYL ESTER;LBYWWJUIABXSBG-UHFFFAOYSA-N;AC4543;MFCD09965916;SB78053;Methyl 1-aminonaphthalene-4-carboxylate;methyl 4-amino-1-naphthalenecarboxylate;SY219378;CS-0216017;EN300-321288;1-NaphthalenecarboxyLIC ACID,4-amino-,methyl ester

Chemical Property of Methyl 4-amino-1-naphthoate

Chemical Property:

• Boiling Point: 400.9±20.0 °C(Predicted)
• PKA: 2.68±0.10(Predicted)
• PSA: 52.32000
• Density: 1.229±0.06 g/cm3(Predicted)
• LogP: 2.78980
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 201.078978594
• Heavy Atom Count: 15
• Complexity: 242

Purity/Quality:

99% ^*data from raw suppliers

methyl4-aminonaphthalene-1-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1=CC=C(C2=CC=CC=C21)N

Technology Process of Methyl 4-amino-1-naphthoate

There total 9 articles about Methyl 4-amino-1-naphthoate 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: 71.0%

methyl 4-(picolinamido)-1-naphthoate → methyl 4-aminonaphthalene-1-carboxylate (157252-24-9)

Guidance literature:

With sodium hydroxide; In methanol; at 90 ℃; for 12h;

DOI:10.1021/acs.joc.9b01184

Reference yield: 62.0%

2-methoxyfuran (25414-22-6) + benzenecarbothioamide (2227-79-4) → 2-Methoxy-5-phenyl-1H-pyrrole-3-carbaldehyde + methyl 4-aminonaphthalene-1-carboxylate (157252-24-9)

Guidance literature:

In benzene; for 20h; Mechanism; Irradiation; other arenecarbothiamides;

DOI:10.1039/c39940001477

Reference yield: 27.0%

methanol (67-56-1) + 4-Amino-1-naphthoic acid (32018-87-4) → methyl 4-aminonaphthalene-1-carboxylate (157252-24-9)

Guidance literature:

With thionyl chloride; at 50 ℃; Inert atmosphere;

DOI:10.1021/acs.jmedchem.7b01154

upstream raw materials:

2-methoxyfuran

benzenecarbothioamide

methyl furan-3-carboxylate

methyl 2-methyl-3-furancarboxylate

Downstream raw materials:

1-amino-5,6,7,8-tetrahydro-4-naphthoic acid methyl ester

Refernces

• 1、 Oda, Kazuaki,Machida, Minoru. "Benzannulation of Heteroaromatics by Photoreaction of Arenecarbothioamides with 2-Methoxyfuran". . p. 1477 - 1478. Retrieved 1994.
• 2、 Kumar, Sandeep,Pradhan, Sourav,Roy, Subhasish,De, Pinaki Bhusan,Punniyamurthy, Tharmalingam. "Iron-Catalyzed Regioselective Remote C(sp2)-H Carboxylation of Naphthyl and Quinoline Amides". . p. 10481 - 10489. Retrieved 2019/08/20.