Methyl 5-amino-6-hydroxypyridine-3-carboxylate

Base Information

• Chemical Name: Methyl 5-amino-6-hydroxypyridine-3-carboxylate
• CAS No.: 222970-60-7
• Molecular Formula: C₇H₈N₂O₃
• Molecular Weight: 168.152
• European Community (EC) Number: 840-126-0
• DSSTox Substance ID: DTXSID50452055
• Nikkaji Number: J1.071.295E
• Wikidata: Q82272417
• Mol file: 222970-60-7.mol

Synonyms:222970-60-7;Methyl 5-amino-6-hydroxypyridine-3-carboxylate;methyl 5-amino-6-oxo-1,6-dihydropyridine-3-carboxylate;Methyl 5-amino-6-oxo-1H-pyridine-3-carboxylate;METHYL 5-AMINO-6-HYDROXYNICOTINATE;5-Amino-6-oxo-1,6-dihydropyridine-3-carboxylic acid methyl ester;SCHEMBL6300267;SCHEMBL19029214;DTXSID50452055;VBLORHWVTGBGNH-UHFFFAOYSA-N;XIA97060;MFCD11053056;AKOS006230123;AKOS022712334;AB63058;3-amino-5-carbomethoxy-1H-pyridin-2-one;5-Amino-6-hydroxynicotinic acid methyl ester;CS-0377027;5-Amino-6-hydroxy-nicotinic acid methyl ester;EN300-41900;F30140;methyl5-amino-6-oxo-1,6-dihydropyridine-3-carboxylate;Z425364744

Chemical Property of Methyl 5-amino-6-hydroxypyridine-3-carboxylate

Chemical Property:

• PSA: 85.44000
• LogP: 0.73720
• XLogP3: -0.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 168.05349212
• Heavy Atom Count: 12
• Complexity: 291

Purity/Quality:

99%min ^*data from raw suppliers

methyl5-amino-6-oxo-1,6-dihydropyridine-3-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1=CNC(=O)C(=C1)N

Technology Process of Methyl 5-amino-6-hydroxypyridine-3-carboxylate

There total 4 articles about Methyl 5-amino-6-hydroxypyridine-3-carboxylate 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:

5-carbomethoxy-3-nitro-1H-pyridin-2-one (222970-61-8) → 3-amino-5-carbomethoxy-1H-pyridin-2-one (222970-60-7)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; for 23h; Yield given;

DOI:10.1016/S0040-4039(98)02628-8

Reference yield:

6-hydroxy-3-pyridinecarboxylic acid (5006-66-6) → 3-amino-5-carbomethoxy-1H-pyridin-2-one (222970-60-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 48 percent / red fuming HNO₃ / 70 - 80 °C

2: pyridine, SOCl₂ / acetonitrile / 2 h / Heating

3: Et₃N / acetonitrile / 2 h / Ambient temperature

4: H₂ / 10 percent Pd/C / aq. ethanol / 23 h

With pyridine; thionyl chloride; hydrogen; nitric acid; triethylamine; palladium on activated charcoal; In ethanol; acetonitrile;

DOI:10.1016/S0040-4039(98)02628-8

Reference yield:

6-hydroxy-5-nitronicotinic acid (6635-31-0) → 3-amino-5-carbomethoxy-1H-pyridin-2-one (222970-60-7)

Guidance literature:

Multi-step reaction with 3 steps

1: pyridine, SOCl₂ / acetonitrile / 2 h / Heating

2: Et₃N / acetonitrile / 2 h / Ambient temperature

3: H₂ / 10 percent Pd/C / aq. ethanol / 23 h

With pyridine; thionyl chloride; hydrogen; triethylamine; palladium on activated charcoal; In ethanol; acetonitrile;

DOI:10.1016/S0040-4039(98)02628-8

upstream raw materials:

5-carbomethoxy-3-nitro-1H-pyridin-2-one

6-hydroxy-3-pyridinecarboxylic acid

6-hydroxy-5-nitronicotinic acid

Refernces