Ethyl 2-amino-4,5-bis(2-methoxyethoxy)benzoate

Base Information

• Chemical Name: Ethyl 2-amino-4,5-bis(2-methoxyethoxy)benzoate
• CAS No.: 179688-27-8
• Molecular Formula: C15H23NO6
• Molecular Weight: 313.351
• Hs Code.: 2922509090
• European Community (EC) Number: 700-551-3
• DSSTox Substance ID: DTXSID20463153
• Wikidata: Q72473029
• Mol file: 179688-27-8.mol

Synonyms:179688-27-8;Ethyl 2-amino-4,5-bis(2-methoxyethoxy)benzoate;Ethyl 4,5-bis(2-methoxyethoxy)-2-aminobenzoate;Benzoic acid, 2-amino-4,5-bis(2-methoxyethoxy)-, ethyl ester;ethyl4,5-bis(2-methoxyethoxy)-2-aminobenzoate;2-amino-4,5-bis(2-methoxyethoxy)benzoic acid ethyl ester;Ethyl 4,5-bis-(2-methoxyethoxy)-2-aminobenzoate;MFCD11618122;C15H23NO6;EC 700-551-3;SCHEMBL264389;DTXSID20463153;YZOWMIHUDJVXBH-UHFFFAOYSA-N;BCP26353;AKOS015888610;AC-8519;FD16018;DS-17935;SY111017;ethyl 4,5-bis(2-methoxyethoxy)anthranilate;AM20090626;CS-0100395;FT-0651481;NS00005826;ethyl2-amino-4,5-bis(2-methoxyethoxy)benzoate;A812477;ethyl 2-amino-4,5-bis(2-methoxyethoxy)-benzoate;2-Amino-4,5-bis(2-methoxyethoxy)benzoic acid ester;2-amino-4,5-bis-(2-methoxy-ethoxy)-benzoic acid ethyl ester

Chemical Property of Ethyl 2-amino-4,5-bis(2-methoxyethoxy)benzoate

Chemical Property:

• Vapor Pressure: 1.62E-08mmHg at 25°C
• Refractive Index: 1.514
• Boiling Point: 456.4 °C at 760 mmHg
• PKA: 2.52±0.10(Predicted)
• Flash Point: 183.9 °C
• PSA: 89.24000
• Density: 1.148 g/cm³
• LogP: 2.07710
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 11
• Exact Mass: 313.15253745
• Heavy Atom Count: 22
• Complexity: 314

Purity/Quality:

99%, ^*data from raw suppliers

2-Amino-4,5-bis(2-methoxyethoxy)benzoicAcidEthylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=CC(=C(C=C1N)OCCOC)OCCOC
• Uses: 2-Amino-4,5-bis(2-methoxyethoxy)benzoic Acid Ethyl Ester is an intermediate in the synthesis of Erlotinib (E625000, HCl); a selective epidermal growth factor receptor (EGFR)-tyrosine kinase inhibitor and antineoplastic agent.

Technology Process of Ethyl 2-amino-4,5-bis(2-methoxyethoxy)benzoate

There total 6 articles about Ethyl 2-amino-4,5-bis(2-methoxyethoxy)benzoate 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: 99.0%

2-nitro-4,5-bis(2-methoxyethoxy)benzoic acid ethyl ester (179688-26-7) → ethyl 2-amino-4,5-bis(2-methoxyethoxy)-benzoate (179688-27-8)

Guidance literature:

With hydrazine hydrate; In N,N-dimethyl-formamide; at 100 ℃; for 3h; chemoselective reaction; Green chemistry;

DOI:10.3184/174751917X15005518143041

Reference yield: 92.0%

→ ethyl 2-amino-4,5-bis(2-methoxyethoxy)-benzoate (179688-27-8)

Guidance literature:

Reference yield:

Ethyl protocatechuate (3943-89-3) → ethyl 2-amino-4,5-bis(2-methoxyethoxy)-benzoate (179688-27-8)

Guidance literature:

Multi-step reaction with 3 steps

1: potassium carbonate; tetrabutylammonium iodide / acetone / 120 h / Heating

2: acetic acid; nitric acid / 24 h / 20 °C

3: hydrogen / PtO₂*H₂O / methanol / 20 °C / 2585.74 Torr

With hydrogen; nitric acid; tetra-(n-butyl)ammonium iodide; potassium carbonate; acetic acid; platinum(IV) oxide; In methanol; acetone;

DOI:10.3390/11040286

upstream raw materials:

2-nitro-4,5-bis(2-methoxyethoxy)benzoic acid ethyl ester

Ethyl protocatechuate

3,4-bis(2-methoxyethoxy)benzoic acid ethyl ester

3,4-bis(2-methoxyethoxy)-benzoic acid

Downstream raw materials:

6,7-bis(2-methoxyethoxy)-3,4-dihydroquinazolin-4-one

4-chloro-6,7-bis(2-methoxyethoxy)quinazoline

erlotinib hydrochloride

N'-[2-carbethoxy-4,5-bis(2-methoxyethoxy)phenyl]-N,N-dimethylformamidine

Refernces

• 1、 -. "Method for synthesizing erlotinib intermediate with microchannel reactor". Paragraph 0052; 0062; 0068; 0071-0072; 0082; 0105-0111; 0122. . Retrieved 2018/09/08.
• 2、 Jiang, Yuqin,Suo, Huajun,Zhang, Dandan,Li, Xiyong,Sun, Yamin,Ren, Baoqi,Zhang, Weiwei,Xu, Guiqing. "An efficient method for reduction of nitroaromatic compounds to the corresponding aromatic amines with NH2NH2·H2O catalysed by H2O2-treated activated carbon". . p. 509 - 512. Retrieved 2017/10/03.