2-Acetylaminoisonicotinic acid

Base Information

• Chemical Name: 2-Acetylaminoisonicotinic acid
• CAS No.: 54221-95-3
• Molecular Formula: C8H8N2O3
• Molecular Weight: 180.163
• Hs Code.: 2933399090
• European Community (EC) Number: 867-446-3
• DSSTox Substance ID: DTXSID10396249
• Mol file: 54221-95-3.mol

Synonyms:54221-95-3;2-Acetylaminoisonicotinic acid;2-acetamidopyridine-4-carboxylic acid;2-Acetylamino-isonicotinic acid;2-Acetamidoisonicotinic acid;2-(acetylamino)isonicotinic acid;MFCD00233713;4-PYRIDINECARBOXYLIC ACID, 2-(ACETYLAMINO)-;EC-000.1965;2-Acetamido-isonicotinic acid;AH-011/25003861;SCHEMBL256750;2-(Acetylamino)isonicotinicacid;4-Carboxy-2-acetylaminopyridine;DTXSID10396249;VNQIEKXUBYBTPS-UHFFFAOYSA-N;AKOS000302620;AB05040;CS-W017216;PS-5454;2-acetylamino-4-pyridinecarboxylic acid;2-(acetamido)pyridine-4-carboxylic acid;AC-25220;AM804022;SY032453;2-Acetylamino-isonicotinic acid, AldrichCPR;FT-0678111;EN300-184016;J-400226

Chemical Property of 2-Acetylaminoisonicotinic acid

Chemical Property:

• Vapor Pressure: 1.52E-14mmHg at 25°C
• Melting Point: 286-290 °C
• Refractive Index: 1.628
• Boiling Point: 585.3 °C at 760 mmHg
• PKA: 1.74±0.10(Predicted)
• Flash Point: 307.8 °C
• PSA: 79.29000
• Density: 1.404 g/cm³
• LogP: 0.81120
• Storage Temp.: Inert atmosphere,Room Temperature
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 180.05349212
• Heavy Atom Count: 13
• Complexity: 217

Purity/Quality:

99.0%Min ^*data from raw suppliers

2-Acetylamino-isonicotinic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)NC1=NC=CC(=C1)C(=O)O
• Uses: 2-Acetylaminoisonicotinic Acid is a reactant in the preparation of nicotinic acid analogues as potent-hypoxia inducible factor (HIF)-1α inhibitors.

Technology Process of 2-Acetylaminoisonicotinic acid

There total 6 articles about 2-Acetylaminoisonicotinic 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: 67.0%

methyl 2-aminoisonicotinate (6937-03-7) + acetyl chloride (75-36-5) → 2-(acetylamino)isonicotinic acid (54221-95-3)

Guidance literature:

methyl 2-aminoisonicotinate; acetyl chloride; With potassium carbonate; In tetrahydrofuran; at 20 ℃; for 24h; Cooling with ice; Inert atmosphere;

With lithium hydroxide; In tetrahydrofuran; methanol; water; at 0 - 20 ℃; for 6h;

DOI:10.1016/j.ejmech.2021.113663

Reference yield: 60.0%

2-aminoisonicotinic acid (13362-28-2) + acetic anhydride (108-24-7) → 2-(acetylamino)isonicotinic acid (54221-95-3)

Guidance literature:

With sulfuric acid; In water; at 90 ℃;

DOI:10.1021/jm5006034

Reference yield: 42.0%

2-acetylamino-4-methylpyridine (5327-32-2) → 2-(acetylamino)isonicotinic acid (54221-95-3)

Guidance literature:

With potassium permanganate; In water; at 50 - 90 ℃; for 2.5h;

DOI:10.1021/jo026619w

upstream raw materials:

2-acetylamino-4-methylpyridine

2-Amino-4-methylpyridine

2-aminoisonicotinic acid

acetic anhydride

Downstream raw materials:

2-amino-5-nitropyridine-4-carboxylic acid

N-(4-aminopyridin-2-yl)acetamide

N-{4-[5-(4-fluoro-phenyl)-3-methyl-2-methylsulfinyl-3H-imidazol-4-yl]-pyridin-2-yl}-acetamide

C₁₇H₁₅FN₄OS

Refernces

• 1、 Okawa, Tomohiro,Aramaki, Yoshio,Yamamoto, Mitsuo,Kobayashi, Toshitake,Fukumoto, Shoji,Toyoda, Yukio,Henta, Tsutomu,Hata, Akito,Ikeda, Shota,Kaneko, Manami,Hoffman, Isaac D.,Sang, Bi-Ching,Zou, Hua,Kawamoto, Tetsuji. "Design, Synthesis, and Evaluation of the Highly Selective and Potent G-Protein-Coupled Receptor Kinase 2 (GRK2) Inhibitor for the Potential Treatment of Heart Failure". . p. 6942 - 6990. Retrieved 2017/09/07.
• 2、 Freitag, Anne,Prajwal, Prajwal,Shymanets, Aliaksei,Harteneck, Christian,Nürnberg, Bernd,Sch?chtele, Christoph,Kubbutat, Michael,Totzke, Frank,Laufer, Stefan A.. "Development of first lead structures for phosphoinositide 3-kinase-c2γ inhibitors". supporting information. p. 212 - 221. Retrieved 2015/03/03.