Methyl 2-amino-4-(benzyloxy)-5-methoxybenzoate

Base Information

• Chemical Name: Methyl 2-amino-4-(benzyloxy)-5-methoxybenzoate
• CAS No.: 61032-42-6
• Molecular Formula: C16H17NO4
• Molecular Weight: 287.315
• Hs Code.: 2922509090
• DSSTox Substance ID: DTXSID60455173
• Nikkaji Number: J1.135.481E
• Wikidata: Q72486706
• Mol file: 61032-42-6.mol

Synonyms:Methyl 2-amino-4-(benzyloxy)-5-methoxybenzoate;61032-42-6;Methyl 2-amino-4-benzyloxy-5-methoxybenzoate;methyl 2-amino-5-methoxy-4-phenylmethoxybenzoate;MFCD16620533;2-Amino-4-benzyloxy-5-methoxy-benzoic acid methyl ester;methyl 2-amino-4-benzyloxy-5-methoxy-benzoate;Methyl2-amino-4-(benzyloxy)-5-methoxybenzoate;SCHEMBL1892032;DTXSID60455173;CKHQUPXMMAOBTC-UHFFFAOYSA-N;CS-M0195;Benzoic acid, 2-amino-5-methoxy-4-(phenylmethoxy)-, methyl ester;AKOS016005076;DS-2504;SB82234;AC-25060;AM807844;FT-0757931;A849206;2-Amino-4-(benzyloxy)-5-methoxybenzoic acid methyl ester

Chemical Property of Methyl 2-amino-4-(benzyloxy)-5-methoxybenzoate

Chemical Property:

• Melting Point: 131-132℃
• Boiling Point: 450.038 °C at 760 mmHg
• PKA: 2.67±0.10(Predicted)
• Flash Point: 199.203 °C
• PSA: 70.78000
• Density: 1.206 g/cm³
• LogP: 3.22420
• Storage Temp.: 2-8°C(protect from light)
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 287.11575802
• Heavy Atom Count: 21
• Complexity: 330

Purity/Quality:

98%,99%, ^*data from raw suppliers

Methyl2-Amino-4-benzyloxy-5-methoxybenzoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=C(C(=C1)C(=O)OC)N)OCC2=CC=CC=C2
• Uses: Methyl 2-Amino-4-benzyloxy-5-methoxybenzoate can be used as reactant/reagent in preparation of cyanoquinolines as protein tyrosine kinase inhibitors.

Technology Process of Methyl 2-amino-4-(benzyloxy)-5-methoxybenzoate

There total 13 articles about Methyl 2-amino-4-(benzyloxy)-5-methoxybenzoate 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: 99.4%

methyl 4-(benzyloxy)-5-methoxy-2-nitrobenzoate (61032-41-5) → methyl 2-amino-4-(benzyloxy)-5-methoxybenzoate (61032-42-6)

Guidance literature:

With iron; ammonium chloride; In methanol; water; at 80 ℃; for 0.5h; Inert atmosphere;

Reference yield: 98.0%

methyl 4-benzyloxy-5-methoxy-2-azidobenzoate → methyl 2-amino-4-(benzyloxy)-5-methoxybenzoate (61032-42-6)

Guidance literature:

With boron trifluoride diethyl etherate; ethanethiol; In dichloromethane; at 20 ℃; for 1.5h;

DOI:10.1016/j.tetlet.2006.04.025

Reference yield: 96.0%

4-Benzyloxy-2-tert-butoxycarbonylamino-5-methoxy-benzoic acid methyl ester → methyl 2-amino-4-(benzyloxy)-5-methoxybenzoate (61032-42-6)

Guidance literature:

With aluminium trichloride; In dichloromethane; for 2h; Ambient temperature;

DOI:10.1055/s-1999-3694

upstream raw materials:

methyl 4-(benzyloxy)-5-methoxy-2-nitrobenzoate

4-(benzyloxy)-3-methoxybenzoic acid

methyl 4-(benzyloxy)-3-methoxybenzoate

4-hydroxy-3-methoxybenzoic acid methyl ester

Downstream raw materials:

2-amino-4-benzyloxy-5-methoxybenzoic acid

2-(allyl-trifluoroacetyl)-amino-4-benzyloxy-N-3-(bromopropyl)-5-methoxy-benzamide

8-benzyloxy-4-(3-bromopropyl)-7-methoxy-1-trifluoroacetyl-1,4-dihydrobenzo[e][1,4]diazepin-5-one

N-allyl-7-benzyloxy-6-methoxyisatoic anhydride

Refernces

• 1、 Zhuo, Lin-Sheng,Wu, Feng-Xu,Wang, Ming-Shu,Xu, Hong-Chuang,Yang, Fan-Peng,Tian, Yan-Guang,Zhao, Xing-E.,Ming, Zhi-Hui,Zhu, Xiao-Lei,Hao, Ge-Fei,Huang, Wei. "Structure–activity relationship study of novel quinazoline-based 1,6-naphthyridinones as MET inhibitors with potent antitumor efficacy". . . Retrieved 2020/09/09.
• 2、 Sundriyal, Sandeep,Chen, Patty B.,Lubin, Alexandra S.,Lueg, Gregor A.,Li, Fengling,White, Andrew J. P.,Malmquist, Nicholas A.,Vedadi, Masoud,Scherf, Artur,Fuchter, Matthew J.. "Histone lysine methyltransferase structure activity relationships that allow for segregation of G9a inhibition and anti-Plasmodium activity". supporting information. p. 1069 - 1092. Retrieved 2017/07/12.