| Identification | Back Directory | [Name]
5-AMINO-NICOTINIC ACID METHYL ESTER | [CAS]
36052-25-2 | [Synonyms]
METHYL 5-AMINONICOTINATE
5-AMINO-NICOTINIC ACID METHYL ESTER
methyl 5-aminopyridine-3-carboxylate
Methyl 5-amino-3-pyridinecarboxylate
Methyl 5-aminopyridine-3-carboxylate ,98%
3-Pyridinecarboxylicacid,5-amino-,methylester
5-Aminopyridine-3-carboxylic acid methyl ester
5-Aminopyridine-3-carboxylic acid methyl ester ,98%
5-AMINO-NICOTINIC ACID METHYL ESTER ISO 9001：2015 REACH | [Molecular Formula]
C7H8N2O2 | [MDL Number]
MFCD04038688 | [MOL File]
36052-25-2.mol | [Molecular Weight]
152.15 |
| Chemical Properties | Back Directory | [Melting point ]
135-137℃ | [Boiling point ]
319.4±22.0 °C(Predicted) | [density ]
1.238 | [storage temp. ]
2-8°C | [form ]
solid | [pka]
4.13±0.20(Predicted) | [Appearance]
Light brown to yellow Solid | [BRN ]
128569 | [InChI]
InChI=1S/C7H8N2O2/c1-11-7(10)5-2-6(8)4-9-3-5/h2-4H,8H2,1H3 | [InChIKey]
MBGSRKHDEJNWED-UHFFFAOYSA-N | [SMILES]
C1=NC=C(N)C=C1C(OC)=O |
| Hazard Information | Back Directory | [Chemical Properties]
Off-white solid | [Synthesis]
SOCl2 (10.4 g, 86.9 mmol) was slowly added dropwise to a stirred methanolic solution (100 mL) of 5-aminonicotinic acid (10.0 g, 72.5 mmol) at 0 °C. After gradually warming the reaction mixture to room temperature, the reaction was continued at reflux for 16 hours. After completion of the reaction, the mixture was cooled and concentrated under vacuum. The residue was diluted with deionized water (200 mL) and subsequently neutralized with aqueous NaHCO3 to pH=7. The aqueous phase mixture was extracted with dichloromethane (DCM, 100 mL x 2). The organic layers were combined, washed with saturated saline (100 mL × 2), dried over anhydrous Na2SO4, filtered, and the filtrate was concentrated to dryness under vacuum to give 9.5 g of methyl 5-aminopyridine-3-carboxylate as a white solid in 86% yield. The product was characterized by 1H NMR (DMSO-d6, 400 MHz): δ=8.24 (1H, d), 8.12 (1H, d), 7.42 (1H, dd), 5.65 (2H, brs), 3.84 (3H, s). | [References]
[1] Patent: WO2013/126608, 2013, A1. Location in patent: Paragraph 00492-00493
[2] Patent: WO2006/117549, 2006, A1. Location in patent: Page/Page column 97
[3] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 22, p. 6305 - 6310
[4] Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 17, p. 6340 - 6350
[5] Chemistry - A European Journal, 2002, vol. 8, # 5, p. 1218 - 1226 |
|
|