Methyl 3-amino-4-hydroxy-5-methoxybenzoate

Base Information

• Chemical Name: Methyl 3-amino-4-hydroxy-5-methoxybenzoate
• CAS No.: 92643-72-6
• Molecular Formula: C9H11NO4
• Molecular Weight: 197.191
• Hs Code.: 2922509090
• DSSTox Substance ID: DTXSID50539850
• Wikidata: Q82415662
• Mol file: 92643-72-6.mol

Synonyms:Methyl 3-amino-4-hydroxy-5-methoxybenzoate;92643-72-6;Methyl 3-amino-4-hydroxy-5-methoxybenzenecarboxylate;MFCD12913545;SCHEMBL751242;3-Amino-4-hydroxy-5-methoxybenzoic acid methyl ester;DTXSID50539850;VISBFCKPNAZKDH-UHFFFAOYSA-N;AC7301;AKOS005071768;AE-0044;SY059761;Methyl3-amino-4-hydroxy-5-methoxybenzoate;CS-0370449;EN300-1082135;J-522137;METHYL 3-AMINO-4-HYDROXY-5-METHOXYBENZOATE 95+%

Chemical Property of Methyl 3-amino-4-hydroxy-5-methoxybenzoate

Chemical Property:

• PSA: 81.78000
• LogP: 1.35080
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 197.06880783
• Heavy Atom Count: 14
• Complexity: 209

Purity/Quality:

97% ^*data from raw suppliers

Methyl 3-amino-4-hydroxy-5-methoxybenzoate 95.0% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC(=CC(=C1O)N)C(=O)OC

Technology Process of Methyl 3-amino-4-hydroxy-5-methoxybenzoate

There total 5 articles about Methyl 3-amino-4-hydroxy-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: 96.0%

4-hydroxy-3-methoxy-5-nitrobenzoic acid methyl ester (42590-00-1) → 3-amino-4-hydroxy-5-methoxybenzoic acid methyl ester (92643-72-6)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In tetrahydrofuran; methanol; at 20 ℃; for 48h; under 760.051 Torr;

DOI:10.1021/acs.jmedchem.0c01035

Reference yield: 28.8%

4-hydroxy-3-methoxybenzoic acid methyl ester (3943-74-6) → methyl 2-amino-4-hydroxy-5-methoxybenzoate (848092-84-2) + 3-amino-4-hydroxy-5-methoxybenzoic acid methyl ester (92643-72-6)

Guidance literature:

With O-(4-nitrobenzoyl)hydroxylammonium trifluoromethanesulfonate; iron(II) bromide; silver(I) triflimide; In 2,2,2-trifluoroethanol; water; at 30 ℃; for 2h;

DOI:10.1002/chem.201605476

Reference yield:

3-methoxy-4-hydroxybenzoic acid (121-34-6) → 3-amino-4-hydroxy-5-methoxybenzoic acid methyl ester (92643-72-6)

Guidance literature:

Multi-step reaction with 3 steps

1: thionyl chloride / 2 h / 0 °C / Reflux; Inert atmosphere

2: acetic acid; nitric acid / 0.25 h / 20 °C / Inert atmosphere

3: hydrogen; palladium 10% on activated carbon / methanol; tetrahydrofuran / 48 h / 20 °C / 760.05 Torr

With thionyl chloride; palladium 10% on activated carbon; hydrogen; nitric acid; acetic acid; In tetrahydrofuran; methanol;

DOI:10.1021/acs.jmedchem.0c01035

upstream raw materials:

4-hydroxy-3-methoxybenzoic acid methyl ester

3-methoxy-4-hydroxybenzoic acid

4-hydroxy-3-methoxy-5-nitrobenzoic acid methyl ester

Downstream raw materials:

8-methoxy-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazine-6-carboxylic acid methyl ester