Methyl 2-aminonicotinate

Base Information

• Chemical Name: Methyl 2-aminonicotinate
• CAS No.: 14667-47-1
• Molecular Formula: C7H8N2O2
• Molecular Weight: 152.153
• Hs Code.: 2933399090
• Mol file: 14667-47-1.mol

Synonyms:Nicotinicacid, 2-amino-, methyl ester (7CI,8CI);2-Amino-3-methoxycarbonylpyridine;2-Amino-3-pyridinecarboxylic acid methyl ester;2-Aminonicotinic acid methylester;Methyl 2-amino-3-pyridinecarboxylate;NSC522516;

Chemical Property of Methyl 2-aminonicotinate

Chemical Property:

• Vapor Pressure: 0.0206mmHg at 25°C
• Melting Point: 84-86 °C
• Refractive Index: 1.57
• Boiling Point: 251.3 °C at 760 mmHg
• PKA: 4.71±0.36(Predicted)
• Flash Point: 105.8 °C
• PSA: 65.21000
• Density: 1.238 g/cm³
• LogP: 1.03160
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility.: soluble in Methanol

Purity/Quality:

Methyl 2-Aminonicotinate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 22-26-36/37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Uses: Methyl 2-Aminonicotinate is used to prepare 2-{4-[(3S)-Piperidin-3-yl]phenyl}-2H-indazole-7-carboxamide (MK-4827)as a novel oral poly(ADP-ribose)polymerase (PARP) inhibitor efficacious in BRCA-1 and -2 mutant tumors. It is also used to synthesize quinazolinone/quinazoline thione derivatives as phosphodiesterase 7 inhibitors.

Technology Process of Methyl 2-aminonicotinate

There total 11 articles about Methyl 2-aminonicotinate 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: 95.0%

2-aminopyridin-3-carboxylic acid (5345-47-1) + diazomethyl-trimethyl-silane (18107-18-1) → methyl 2-aminonicotinate (14667-47-1)

Guidance literature:

In methanol; toluene; at 0 ℃; for 0.5h;

DOI:10.1080/14756366.2018.1516652

Reference yield: 94.0%

2-aminopyridin-3-carboxylic acid (5345-47-1) + 2-chloro-1,3-dimethyl imidazolium chloride → methyl 2-aminonicotinate (14667-47-1)

Guidance literature:

With triethylamine; In methanol; at 20 ℃; for 1h;

Reference yield: 93.0%

methanol (67-56-1) + 2-aminopyridin-3-carboxylic acid (5345-47-1) → methyl 2-aminonicotinate (14667-47-1)

Guidance literature:

With sulfuric acid; at 0 - 60 ℃; for 1.5h; under 760.051 Torr; Inert atmosphere; Microwave irradiation;

DOI:10.1016/j.tet.2014.06.103

upstream raw materials:

methanol

2-aminopyridin-3-carboxylic acid

diazomethane

2-chloro-1,3-dimethylimidazolinium chloride

Downstream raw materials:

N-(3-methoxycarbonyl-2-pyridyl)triphenyliminophosphorane

methyl 8-imidazo<1,2-a>pyridinecarboxylate

2-[2-(2,4-dichloro-phenyl)-acetylamino]-nicotinic acid methyl ester

4-amino-6-((2,4-diphenyl-1,8-naphthyridin-3-yl)methylamino)pyrimidine-5-carbonitrile

Refernces

• 1、 Bay, Katherine L.,Chen, Xiangyang,Fan, Zhoulong,Houk, K. N.,Park, Han Seul,Yeung, Kap-Sun,Yu, Jin-Quan,Zhuang, Zhe. "Rational Development of Remote C?H Functionalization of Biphenyl: Experimental and Computational Studies". . p. 4770 - 4777. Retrieved 2020.
• 2、 Ballet, Steven,Elsocht, Mathias,Hollanders, Charlie,Jida, Mouhamad,Maes, Bert U. W.,Renders, Evelien,Van der Poorten, Olivier. "3-Substituted 2-isocyanopyridines as versatile convertible isocyanides for peptidomimetic design". supporting information. p. 6863 - 6866. Retrieved 2021/07/19.
• 3、 Ronson, Thomas O.,Renders, Evelien,Van Steijvoort, Ben F.,Wang, Xubin,Wybon, Clarence C. D.,Prokopcová, Hana,Meerpoel, Lieven,Maes, Bert U. W.. "Ruthenium-Catalyzed Reductive Arylation of N-(2-Pyridinyl)amides with Isopropanol and Arylboronate Esters". supporting information. p. 482 - 487. Retrieved 2019/01/04.