| Identification | Back Directory | [Name]
2-ACETYLAMINO-ISONICOTINIC ACID | [CAS]
54221-95-3 | [Synonyms]
Zinc02559887
2-AcetylaMino-isonic acid
2-ACETAMIDOISONICOTINIC ACID
2-ACETYLAMINO-ISONICOTINIC ACID
2-acetamido-4-pyridinecarboxylate
2-(Acetylamino)isonicotinicacid97%
2-(Acetylamino)isonicotinic acid 97%
2-Acetamido-4-pyridinecarboxylic acid
2-AECTAMIDO-4-PYRIDINECARBOXYLIC ACID
2-acetaMidopyridine-4-carboxylic acid
2-(Acetylamino)pyridine-4-carboxylic acid
4-Pyridinecarboxylic acid, 2-(acetylamino)- | [Molecular Formula]
C8H8N2O3 | [MDL Number]
MFCD00233713 | [MOL File]
54221-95-3.mol | [Molecular Weight]
180.16 |
| Chemical Properties | Back Directory | [Melting point ]
286-290 | [Boiling point ]
585.3±35.0 °C(Predicted) | [density ]
1.404±0.06 g/cm3(Predicted) | [storage temp. ]
Inert atmosphere,Room Temperature | [form ]
Solid | [pka]
1.74±0.10(Predicted) | [Appearance]
White to light yellow Solid |
| Hazard Information | Back Directory | [Uses]
2-Acetylaminoisonicotinic Acid is a reactant in the preparation of nicotinic acid analogues as potent-hypoxia inducible factor (HIF)-1α inhibitors. | [Synthesis]
b) Synthesis of 2-acetamido pyridine-4-carboxylic acid (3): 214.0 g of 2-(acetamido)-4-methylpyridine (2) was added in batches to an aqueous solution of 160 g of potassium permanganate at 50 °C while maintaining stirring. An additional 360 g of potassium permanganate was added in batches over a period of 1 hour, during which the temperature of the reaction mixture needed to be controlled not to exceed 90 °C. After completion of the reaction, stirring was continued for 1.5 hours, followed by thermal filtration. The pH of the filtrate was adjusted to 3-4 with concentrated hydrochloric acid, and the white precipitate precipitated was 2-acetylaminopyridine-4-carboxylic acid (3). After separation by filtration and drying under vacuum conditions, 108.0 g of product was obtained in 42% yield. | [References]
[1] Journal of Organic Chemistry, 2003, vol. 68, # 11, p. 4527 - 4530
[2] Patent: WO2006/89798, 2006, A1. Location in patent: Page/Page column 25
[3] Patent: EP1894925, 2008, A1. Location in patent: Page/Page column 14; 41
[4] Journal of Medicinal Chemistry, 2017, vol. 60, # 16, p. 6942 - 6990
[5] Farmaco, Edizione Scientifica, 1958, vol. 13, p. 485,487 |
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