2-Amino-6-methoxynicotinic acid

Base Information

• Chemical Name: 2-Amino-6-methoxynicotinic acid
• CAS No.: 1196156-84-9
• Molecular Formula: C₇H₈N₂O₃
• Molecular Weight: 168.152
• DSSTox Substance ID: DTXSID70695942
• Wikidata: Q82625333
• Mol file: 1196156-84-9.mol

Synonyms:2-AMINO-6-METHOXYNICOTINIC ACID;1196156-84-9;2-amino-6-methoxypyridine-3-carboxylic acid;2-AMINO-6-METHOXY-NICOTINIC ACID;3-Pyridinecarboxylic acid, 2-amino-6-methoxy-;SCHEMBL21339634;DTXSID70695942;WXB15684;MFCD13190079;2-AMINO-6-METHOXYNICOTINICACID;AB69714;AC-29549;AS-78157;CS-0150241;FT-0705701;F31118;A892496;J-400241

Chemical Property of 2-Amino-6-methoxynicotinic acid

Chemical Property:

• Storage Temp.: 2-8°C(protect from light)
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 168.05349212
• Heavy Atom Count: 12
• Complexity: 174

Purity/Quality:

98%min ^*data from raw suppliers

2-Amino-6-methoxynicotinicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=NC(=C(C=C1)C(=O)O)N

Technology Process of 2-Amino-6-methoxynicotinic acid

There total 8 articles about 2-Amino-6-methoxynicotinic acid 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: 77.0%

methyl 2-amino-6-methoxynicotinate (1227048-93-2) → 2-amino-6-methoxynicotinic acid (1196156-84-9)

Guidance literature:

With water; lithium hydroxide; In tetrahydrofuran; methanol; at 27 ℃; for 16h;

Reference yield:

2-chloro-6-methoxypyridine-3-carboxylic acid (503000-87-1) → 2-amino-6-methoxynicotinic acid (1196156-84-9)

Guidance literature:

Multi-step reaction with 4 steps

1: thionyl chloride / 16 h / 0 - 80 °C

2: potassium carbonate / N,N-dimethyl-formamide / 10 h / 0 - 100 °C

3: palladium on activated charcoal; hydrogen / ethanol / 16 h / 27 °C / Inert atmosphere

4: lithium hydroxide; water / tetrahydrofuran; methanol / 16 h / 27 °C

With thionyl chloride; palladium on activated charcoal; water; hydrogen; potassium carbonate; lithium hydroxide; In tetrahydrofuran; methanol; ethanol; N,N-dimethyl-formamide;

Reference yield:

methyl 2-chloro-6-methoxynicotinate hydrochloride → 2-amino-6-methoxynicotinic acid (1196156-84-9) + 2-chloro-6-methoxynicotinamide (1261079-74-6) + C7H9N3O2 (1298123-77-9)

Guidance literature:

With ammonium hydroxide; In ethanol; at 100 ℃; for 5h; Microwave irradiation;

DOI:10.1055/s-0030-1259283

upstream raw materials:

sodium methylate

2-amino-6-chloronicotinic acid

methanol

2,6-dichloropyridine-3-carboxylic acid

Downstream raw materials:

C₁₄H₁₂N₄O₂

Refernces

• 1、 -. "INHIBITORS OF HUMAN IMMUNODEFICIENCY VIRUS REPLICATION". . . Retrieved 2020/06/01.
• 2、 Jeges, Gyorgy,Meszaros, Tamas,Szommer, Tamas,Kovacs, Jozsef,Nagy, Tamas,Tymoshenko, Dmytro,Fotouhi, Nader,Gillespie, Paul,Kowalczyk, Agnieszka,Goodnow Jr., Robert A.. "First synthesis of methyl 2-amino-6-methoxynicotinate using a combination of microwave and flow reaction technologies". scheme or table. p. 203 - 206. Retrieved 2011/03/22.