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Ethyl 2-aminopyridine-3-carboxylate

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CAS:13362-26-0
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Ethyl 2-aminopyridine-3-carboxylate manufacturers

Ethyl 2-aminopyridine-3-carboxylate Basic information
Product Name:Ethyl 2-aminopyridine-3-carboxylate
Synonyms:Ethyl 2-aMinonicotinic acid;Nicotinic acid Impurity 10;RARECHEM AL BI 1234;AKOS 90517;Ethyl 2-amino-3-pyridinecarboxylate;ethyl 2-aMinopyridin-3-carboxylate;Ethyl 2-aminonicotinate ,97%;2-Amino-3-(ethoxycarbonyl)pyridine
CAS:13362-26-0
MF:C8H10N2O2
MW:166.18
EINECS:
Product Categories:Amines;Heterocycles;pharmacetical;API intermediates;Pyridine
Mol File:13362-26-0.mol
Ethyl 2-aminopyridine-3-carboxylate Structure
Ethyl 2-aminopyridine-3-carboxylate Chemical Properties
Melting point 96-98°C
Boiling point 133°C/12mmHg(lit.)
density 1.192±0.06 g/cm3(Predicted)
storage temp. Keep in dark place,Inert atmosphere,Room temperature
solubility DMSO, Methanol
form Solid
pka4.84±0.36(Predicted)
color Yellow
InChIInChI=1S/C8H10N2O2/c1-2-12-8(11)6-4-3-5-10-7(6)9/h3-5H,2H2,1H3,(H2,9,10)
InChIKeyKIAGEDYOPMHRRB-UHFFFAOYSA-N
SMILESC1(N)=NC=CC=C1C(OCC)=O
CAS DataBase Reference13362-26-0(CAS DataBase Reference)
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 26-36/37/39
HazardClass IRRITANT
HS Code 29339900
MSDS Information
Ethyl 2-aminopyridine-3-carboxylate Usage And Synthesis
Chemical PropertiesYellow Solid
UsesA pyrimidine derivative with diuretic activity.
Synthesis
2-Aminonicotinic acid

5345-47-1

Ethanol

64-17-5

Ethyl 2-aminopyridine-3-carboxylate

13362-26-0

2-Aminonicotinic acid (1) (5 g, 36 mmol) and ethanol (100 mL) were used as feedstock to which concentrated sulfuric acid (10 mL) was added. The reaction mixture was heated to reflux for 16 hours and subsequently cooled to room temperature. The completion of the reaction was confirmed by LC-MS analysis. The volatiles were removed under vacuum, water was added, and the crude product was alkalized with 1N NaOH solution to pH 8.0. The product was extracted twice with ethyl acetate, and the organic phases were combined, dried over magnesium sulfate, and then concentrated to afford ethyl (2) 2-aminonicotinate (6.0 g, 100% yield) as a white crystalline solid. hplc-ms analysis results: retention time t R = 0.41 min (UV 254 nm); mass calculated value C8H10N2O2 166.1, measured value LCMS m/z 167.1 (M + H).

References[1] Patent: WO2008/82490, 2008, A2. Location in patent: Page/Page column 70
[2] Patent: TWI525093, 2016, B. Location in patent: Page/Page column 101;
[3] Patent: WO2007/67416, 2007, A2. Location in patent: Page/Page column 64; 134
[4] Patent: WO2007/86080, 2007, A2. Location in patent: Page/Page column 37
[5] Heterocycles, 1993, vol. 36, # 11, p. 2513 - 2522
Ethyl 2-aminopyridine-3-carboxylate Preparation Products And Raw materials
Raw materialsThionyl chloride-->Acetic anhydride-->Benzene-->Potassium permanganate-->2-Amino-3-picoline-->2-Aminonicotinic acid-->Ethanol-->Iodoethane-->Sodium hydroxide
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