Encyclopedia / Pharmaceutical Intermediates / Organic Intermediate

3-Aminopyridine-2-carboxylic acid ethyl ester

CAS：27507-15-9
MW:166.1772
MF：C8H10N2O2

A synthetic intermediate for the synthesis of Kenpaullone derivatives, Cannabinoid receptor ligands, and nociceptive agents. 3-Aminopyridine-2-carboxylic acid ethyl esterSupplier View more+

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Names and ldentifier
Properties
Use and Manufacturing
Other Information
Computational chemical data
Realated Product Infomation

1. Names and Identifiers

1.1 Name: 3-Aminopyridine-2-carboxylic acid ethyl ester

1.2 Synonyms: 2-Pyridinecarboxylic acid, 3-aMino-, ethyl ester; 3-amino-2-ethoxycarbonylpyridine; 3-AMino-2-pyridinecarboxylic Acid Ethyl Ester; 3-Aminopicolinic acid ethyl ester; 3-Amino-picolinic Acid Ethyl Ester; 3-Amino-pyridin-2-carbonsaeure-aethylester; 3-amino-pyridine-2-carboxylic acid ethyl ester; 3-Aminopyridine-2-carboxylic acid ethyl ester ISO 9001：2015 REACH; Ethyl 3-amino-2-pyridinecarboxylate; Ethyl 3-AMinopicolinate; Ethyl 3-Aminopyridine-2-carboxylate; Picolinic acid, 3-amino-, ethyl ester;

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1.3 CAS No.: 27507-15-9

1.4 CID: 565054

1.5 Molecular Formula: C8H10N2O2

1.6 Inchi: InChI=1S/C8H10N2O2/c1-2-12-8(11)7-6(9)4-3-5-10-7/h3-5H,2,9H2,1H3

1.7 InChkey: FKDRDUIRSZRBSN-UHFFFAOYSA-N

1.8 Canonical Smiles: CCOC(=O)C1=C(C=CC=N1)N

1.9 Isomers Smiles: CCOC(=O)C1=C(C=CC=N1)N

2. Properties

2.1 Solubility: 微溶 (8.8 g/L) (25 oC),

2.2 pKa: 2.79±0.10(Predicted)

2.3 StorageTemp: Keep in dark place,Sealed in dry,2-8°C

3. Use and Manufacturing

3.1 Methods of Manufacturing: A suspension of 3-aminopicolinic acid (1-18) (28 g, 200 mmoL, 1.0 eq) in EtOH (800 mL) at room temperature was bubbled with HCI (g) for 10 min. The reaction turned into a clear yellow solution. After being stirred at 100°C for 1 day, LCMS indicated that about 50percent of starting material remained. The reaction mixture was cooled to rt and bubbled with HCI (g) for 10 min. The mixture was then re-heated to 100 °C. After being stirred at 100 °C for 1 day, LCMS indicated that about 50percent of the starting material remained. The reaction mixture was cooled to rt and all solvents were removed under reduced pressure. The residue was resolved in EtOH (800 mL) and was bubbled with HCI (g) for 10 min. The resulting mixture was refluxed at 100°C oil bath for 1 day. LCMS indicated about 70-75 percent conversion. The reaction mixture was cooled to rt and all solvents were removed under reduced pressure. The solid was dissolved in 250 mL water and the solution was quenched to pH = 8-9 with saturated aq Na2C03. A gas was generated and a white solid formed. The suspension was filtered, washed with water, and dried under vacuum at 65°C to afford 22 g of ethyl 3-aminopicolinate (1-19) in 65percent yleld as a white solid. LCMS (APCI, M+ + 1 ) 167.0; 1H NMR (300 MHz, DMSO-c/6) 8 ppm 7.84 (dd, J = 4.05, 1 .60 Hz, 1 H), 7.23 - 7.30 (m, 1 H), 7.16 - 7.23 (m, 1 H), 6.65 (br. s., 2 H), 4.27 (q, J = 7.10 Hz, 2 H), 1 .30 (t, J = 7.06 Hz, 3 H).

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3.2 Usage: A synthetic intermediate for the synthesis of Kenpaullone derivatives, Cannabinoid receptor ligands, and nociceptive agents. 3-Aminopyridine-2-carboxylic acid ethyl esterSupplier

4. Synthesis Route

27507-15-9Total: 3 Synthesis Route

64-17-5 396 Suppliers

1462-86-8 131 Suppliers

27507-15-9 19 Suppliers

462-08-8 179 Suppliers

617-35-6 231 Suppliers

27507-15-9 19 Suppliers

119830-47-6 5 Suppliers

5. Precursor and Product

precursor:

64-17-5

462-08-8

617-35-6

1462-86-8

product:

55234-58-7

28033-08-1

874-24-8

3303-28-4

676596-64-8

655244-89-6

676596-63-7

52378-63-9

676596-62-6

50608-99-6

6. Computed Properties

Molecular Weight：166.1772g/mol
Molecular Formula：C₈H₁₀N₂O₂
Compound Is Canonicalized：True
Exact Mass：1.3
XLogP3-AA：166.074227566
Monoisotopic Mass：166.074227566
Complexity：161
Rotatable Bond Count：3
Hydrogen Bond Donor Count：1
Hydrogen Bond Acceptor Count：4
Topological Polar Surface Area：65.2
Heavy Atom Count：：12
Defined Atom Stereocenter Count：0
Undefined Atom Stereocenter Count：0
Defined Bond Stereocenter Count：0
Undefined Bond Stereocenter Count：0
Isotope Atom Count：0
Covalently-Bonded Unit Count：1
CACTVS Substructure Key Fingerprint：AAADccBzMAAAAAAAAAAAAAAAAAAAAAAAAAAsAAAAAAAAAAABgAAAHgAQAAAACAjhlgY+yJJIFACoATT3TASCgCA3EiAI2CG4fNgKZvrAtbmXMYhm0AHY6UeYSAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==