3-Aminopyridine-2-carboxylic acid ethyl ester
- Iupac Name：ethyl 3-aminopyridine-2-carboxylate
- CAS No.: 27507-15-9
- Molecular Weight：166.1772
- Modify Date.: 2022-11-22 22:05
- Introduction: A synthetic intermediate for the synthesis of Kenpaullone derivatives, Cannabinoid receptor ligands, and nociceptive agents. 3-Aminopyridine-2-carboxylic acid ethyl esterSupplier
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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 (isomer)
- 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 InChIkey
- 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 Density
- 1.192
- 2.1 Melting point
- 131-133 oC
- 2.1 Boiling point
- 326.2°Cat760mmHg
- 2.1 Refractive index
- 1.558
- 2.1 Flash Point
- 151.1°C
- 2.1 Precise Quality
- 166.07400
- 2.1 PSA
- 65.21000
- 2.1 logP
- 1.42170
- 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. Safety and Handling
- 4.1 Hazard Declaration
- H302
- 4.1 Caution Statement
- P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, P501
5. Synthesis Route
27507-15-9Total: 3 Synthesis Route
7. Other Information
- 7.0 Uses
- A synthetic intermediate for the synthesis of Kenpaullone derivatives, Cannabinoid receptor ligands, and nociceptive agents.
8. Computational chemical data
- Molecular Weight: 166.1772g/mol
- Molecular Formula: C8H10N2O2
- Compound Is Canonicalized: True
- XLogP3-AA: 1.3
- Exact Mass: 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==
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