Methyl 2-amino-5-nitronicotinate

Base Information

• Chemical Name: Methyl 2-amino-5-nitronicotinate
• CAS No.: 88312-64-5
• Molecular Formula: C7H7N3O4
• Molecular Weight: 197.14800
• Hs Code.: 2933399090
• DSSTox Substance ID: DTXSID30516907
• Nikkaji Number: J3.377.217C
• Wikidata: Q82378562
• Mol file: 88312-64-5.mol

Synonyms:Methyl 2-amino-5-nitronicotinate;88312-64-5;METHYL 2-AMINO-5-NITROPYRIDINE-3-CARBOXYLATE;2-amino-5-nitronicotinic acid methyl ester;MFCD19441225;2-Amino-5-nitro-nicotinic acid methyl ester;Methyl2-amino-5-nitronicotinate;SCHEMBL1680354;DTXSID30516907;OUMPFIBIUJBCAH-UHFFFAOYSA-N;BCP23417;AKOS015995172;SB52648;s11687;DS-14607;SY271843;CS-0042659;FT-0687607;EN300-2008315

Chemical Property of Methyl 2-amino-5-nitronicotinate

Chemical Property:

• PSA: 111.03000
• LogP: 1.46300
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 197.04365571
• Heavy Atom Count: 14
• Complexity: 240

Purity/Quality:

97% ^*data from raw suppliers

Methyl2-Amino-5-nitronicotinate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1=C(N=CC(=C1)[N+](=O)[O-])N
• Uses: Methyl 2-amino-5-nitronicotinate is a useful chemical for the synthesis of polyfunctionalized benzo[d]thiazole and its aza analog thiazolo[5,4-b]pyridine.

Technology Process of Methyl 2-amino-5-nitronicotinate

There total 4 articles about Methyl 2-amino-5-nitronicotinate 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: 82.0%

methyl 2-aminonicotinate (14667-47-1) → 2-amino-3-(methoxycarbonyl)-5-nitropyridine (88312-64-5)

Guidance literature:

With sulfuric acid; nitric acid; at 0 - 20 ℃; for 2h; regioselective reaction; Inert atmosphere;

DOI:10.1016/j.tet.2014.06.103

Reference yield: 26.0%

5-nitropyrimidine (14080-32-1) + methyl 2-cyanoacetate (105-34-0) → 2-amino-3-(methoxycarbonyl)-5-nitropyridine (88312-64-5) + 3-cyano-5-nitro-2(1H)-pyridone

Guidance literature:

With triethylamine; In ethanol; for 2h; Heating;

Reference yield:

2-aminopyridin-3-carboxylic acid (5345-47-1) → 2-amino-3-(methoxycarbonyl)-5-nitropyridine (88312-64-5)

Guidance literature:

Multi-step reaction with 2 steps

1: sulfuric acid / 1.5 h / 0 - 60 °C / 760.05 Torr / Inert atmosphere; Microwave irradiation

2: sulfuric acid; nitric acid / 2 h / 0 - 20 °C / Inert atmosphere

With sulfuric acid; nitric acid;

DOI:10.1016/j.tet.2014.06.103

upstream raw materials:

5-nitropyrimidine

methyl 2-cyanoacetate

methyl 2-aminonicotinate

2-aminopyridin-3-carboxylic acid