| Identification | More | [Name]
Methyl 2-aminopyridine-4-carboxylate | [CAS]
6937-03-7 | [Synonyms]
CHEMBRDG-BB 4015127
METHYL 2-AMINOISONICOTINATE
METHYL 2-AMINOPYRIDINE-4-CARBOXYLATE
2-Aminopyridinecarboxylic acid methyl ester~Methyl 2-aminoisonicotinate
2-Aminopyridine-4-carboxylic acid methyl ester
2-aminopyridinecarboxylic acid methyl ester
methyl 2-aminoisonicotinate, (2-Amino-4-pyridinecarboxylic acid methylester)
Methyl 2-Amino-4-pyridinecarboxylate
NSC 40138
2-Amniopyridine-4-carboxylic acid methyl ester | [EINECS(EC#)]
627-546-8 | [Molecular Formula]
C7H8N2O2 | [MDL Number]
MFCD04039316 | [Molecular Weight]
152.15 | [MOL File]
6937-03-7.mol |
| Chemical Properties | Back Directory | [Melting point ]
144-148 °C | [Boiling point ]
296.1±20.0 °C(Predicted) | [density ]
1.238±0.06 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Sealed in dry,Room Temperature | [solubility ]
Chloroform | [form ]
Crystalline Powder | [pka]
4.89±0.11(Predicted) | [color ]
White to brown | [Water Solubility ]
Insoluble in water. | [Usage]
A nitrogen monoxide synthetase inhibitor. | [BRN ]
128642 | [InChI]
InChI=1S/C7H8N2O2/c1-11-7(10)5-2-3-9-6(8)4-5/h2-4H,1H3,(H2,8,9) | [InChIKey]
SVWWNEYBEFASMP-UHFFFAOYSA-N | [SMILES]
C1(N)=NC=CC(C(OC)=O)=C1 | [CAS DataBase Reference]
6937-03-7(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [HazardClass ]
IRRITANT | [HS Code ]
29333990 |
| Hazard Information | Back Directory | [Chemical Properties]
Tan Solid | [Uses]
A nitrogen monoxide synthetase inhibitor. | [Synthesis Reference(s)]
The Journal of Organic Chemistry, 72, p. 4554, 2007 DOI: 10.1021/jo070189y | [Synthesis]
The general procedure for the synthesis of methyl 2-aminoisonicotinate from methanol and 2-aminoisonicotinic acid was as follows: 2-aminoisonicotinic acid (207 g, 1.5 mol) was dissolved in methanol (1.8 L) to prepare a solution. The solution was slowly added dropwise to thionyl chloride (238 g, 2 mol) at 50 °C. After the dropwise addition was completed, the reaction temperature was maintained at 50 °C and the reaction mixture continued to be stirred for 5 hours. After completion of the reaction, the solvent was removed by distillation under reduced pressure. To the residue, saturated aqueous sodium carbonate solution was added and the pH was adjusted to 9-10 to make the reaction mixture basic. Subsequently, the mixed solution was extracted with dichloromethane (300 ml each time for 3 times). The organic layers were combined and dried with anhydrous sodium sulfate. Finally, the solvent was removed by concentration to give methyl 2-aminoisonicotinate (189 g, 83% yield) as a yellow solid. The structure of the product was confirmed by 1H-NMR (d6-DMSO, 300 MHz): δ 3.96 (s, 3H); 7.14 (d, 1H); 7.49 (br, 1H); 8.07 (d, 1H); 8.18 (br, 2H, NH). | [References]
[1] European Journal of Medicinal Chemistry, 2013, vol. 61, p. 26 - 40
[2] Journal of the American Chemical Society, 2018, vol. 140, # 9, p. 3322 - 3330
[3] Chemistry - A European Journal, 2012, vol. 18, # 27, p. 8498 - 8507
[4] Patent: EP3018125, 2016, A1. Location in patent: Paragraph 0515-0518
[5] Russian Journal of Organic Chemistry, 2015, vol. 51, # 5, p. 744 - 745 |
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