| Identification | More | [Name]
3-AMINO-ISONICOTINIC ACID ETHYL ESTER | [CAS]
14208-83-4 | [Synonyms]
3-AMINO-4-PYRIDINECARBOXYLIC ACID ETHYL ESTER
3-AMINO-ISONICOTINIC ACID ETHYL ESTER
3-AMINOPYRIDINE-4-CARBOXYLIC ACID ETHYL ESTER
ETHYL 3-AMINOPYRIDINE-4-CARBOXYLATE
Ethyl3-amino-4-pyridinecarboxylate
3-Amino-isonicotinic acid ethyl ester ,98% | [Molecular Formula]
C8H10N2O2 | [MDL Number]
MFCD03788270 | [Molecular Weight]
166.18 | [MOL File]
14208-83-4.mol |
| Chemical Properties | Back Directory | [Melting point ]
170-175 | [Boiling point ]
304.0±22.0 °C(Predicted) | [density ]
1.192±0.06 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Sealed in dry,Room Temperature | [form ]
powder to crystal | [pka]
4.13±0.18(Predicted) | [color ]
Light orange to Yellow to Green | [Detection Methods]
HPLC,NMR | [CAS DataBase Reference]
14208-83-4(CAS DataBase Reference) |
| Hazard Information | Back Directory | [Chemical Properties]
Off-white powder or chunks solid | [Uses]
3-Amino-isonicotinic Acid Ethyl Ester acts as a reagent for the synthetic preparation of heteroaryl compounds as PDE-10 inhibitors useful in treatment and prevention of CNS, metabolic and other diseases. Also in the design and evaluation of 1,7-naphthyridones as novel KDM5 inhibitors. | [Synthesis]
To ethanol (20 mL) was added 3-aminoisonicotinic acid (1.4 g, 10 mmol) and stirred until completely dissolved. Concentrated sulfuric acid (2.94 g, 30 mmol) was added slowly and the reaction was heated to reflux for 20 hours. After completion of the reaction, ethanol was removed by distillation under reduced pressure. To the residue, water was added and the pH was adjusted to 8-9 with 2 N sodium hydroxide solution under cooling in an ice bath. the precipitated solid was filtered and dried to give ethyl 3-aminoisonicotinate (0.70 g, 42% yield). The filtrate was extracted with ethyl acetate, the organic phase was washed sequentially with water and saturated sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure to give additional ethyl 3-aminoisonicotinate (0.30 g, 18% yield). The product was characterized by 1H-NMR (DMSO-d6): δ 1.30 (3H, t, J = 7.1 Hz), 4.28 (2H, q, J = 7.1 Hz), 6.66 (2H, br.s), 7.45 (1H, d, J = 5.2 Hz), 7.73 (1H, d, J = 5.2 Hz), 8.23 (1H, s). | [References]
[1] Australian Journal of Chemistry, 1993, vol. 46, # 7, p. 987 - 993
[2] Patent: EP1844768, 2007, A1. Location in patent: Page/Page column 29-30
[3] Journal of Organic Chemistry, 1952, vol. 17, p. 547,553
[4] Bulletin de la Societe Chimique de France, 1992, # 1, p. 79 - 84
[5] Journal of Medicinal Chemistry, 1993, vol. 36, # 18, p. 2676 - 2688 |
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