Methyl 2-aminonicotinate Chemical Properties

Melting point:

82-86 °C

Boiling point:

251.3±20.0 °C(Predicted)

Density 

1.238±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

soluble in Methanol

form 

powder to crystal

pka

4.71±0.36(Predicted)

color 

White to Almost white

InChI

InChI=1S/C7H8N2O2/c1-11-7(10)5-3-2-4-9-6(5)8/h2-4H,1H3,(H2,8,9)

InChIKey

NZZDEODTCXHCRS-UHFFFAOYSA-N

SMILES

C1(N)=NC=CC=C1C(OC)=O

CAS DataBase Reference

14667-47-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn

Risk Statements 

20/21/22-36/37/38

Safety Statements 

22-26-36/37/39

WGK Germany 

2

HazardClass 

IRRITANT

HS Code 

2933399990

MSDS

• Language:English Provider:ALFA

Methyl 2-aminonicotinate Usage And Synthesis

Chemical Properties

Off white powder

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.

Synthesis

Concentrated sulfuric acid (96%, 144 mL, 2.69 mol, 18.6 eq.) was slowly added dropwise to a stirred suspension of 2-aminonicotinic acid (20.0 g, 0.145 mol) in methanol (228 mL, 7.12 mol, 49.2 eq.), and the reaction system was kept at 0 °C. Subsequently, the reaction mixture was irradiated in a microwave reactor (power input 300 W) at 60 °C and atmospheric pressure for 1.5 hours. Upon completion of the reaction, the light brown mixture was carefully poured into ice water, maintained at 0 °C, and solid sodium carbonate was added by batchwise addition until complete neutralization (pH > 8). The aqueous layer was extracted three times with ethyl acetate. The organic layers were combined, washed sequentially with saturated brine and deionized water, and then dried with anhydrous magnesium sulfate. Finally, the organic solvent was evaporated to afford methyl 2-aminopyridine-3-carboxylate (21.15 g, 93% yield) as colorless needle-like crystals with purity meeting the analytical requirements.

References

[1] Tetrahedron, 2014, vol. 70, # 35, p. 5541 - 5549
[2] European Journal of Medicinal Chemistry, 2012, vol. 52, p. 284 - 294
[3] Synthetic Communications, 2006, vol. 36, # 2, p. 181 - 186
[4] Patent: WO2005/32481, 2005, A2. Location in patent: Page/Page column 38
[5] Patent: WO2005/32481, 2005, A2. Location in patent: Page/Page column 38

Methyl 2-aminonicotinate(14667-47-1)Related Product Information

• Methyl 2-aminonicotinate
• Morniflumate
• Talniflumate
• METHYL 2-AMINOPYRIDINE-4-CARBOXYLATE
• 2-Pyridinecarboxylicacid,5-amino-,methylester(9CI)
• METHYL 3-AMINOPYRIDINE-4-CARBOXYLATE
• Methyl 6-aminopyridine-2-carboxylate,Methyl 6-aminopyridine-2-carboxylate 98%
• Methyl 5-aminopyridine-3-carboxylate ,98%,METHYL 5-AMINONICOTINATE
• Methyl 6-aminonicotinate
• METHYL-4-AMINONICOTINATE,methyl 4-aminopyridine-3-carboxylate
• methyl 3-aminopyridine-2-carboxylate
• Methyl 4-aminopyridine-2-carboxylate
• 2-Aminonicotinic acid
• Methyl nicotinate
• 2-AMINO-QUINOLINE-3-CARBOXYLIC ACID ETHYL ESTER
• Clonixeril
• Methyl 2-(dimethylamino)pyridine-4-carboxylate ,97%
• ISOPROPYL 2-(4-PHENYLPIPERAZINO)NICOTINATE