2-CHLORO-N-PYRIDIN-2-YL-ACETAMIDE Chemical Properties

Melting point:

110 °C

Boiling point:

378.1±22.0 °C(Predicted)

Density 

1.341±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

pka

11.59±0.70(Predicted)

Safety Information

Hazard Codes 

Xi

HazardClass 

IRRITANT

HS Code 

2933399990

2-CHLORO-N-PYRIDIN-2-YL-ACETAMIDE Usage And Synthesis

Synthesis

1. Dissolve 2-aminopyridine (2.8 g, 30 mmol) in 50 mL of ethylene dichloride (25 mL) in a 50 mL glass container. 2. Slowly add chloroacetyl chloride dropwise to the above solution. 3. seal the glass vessel with a TFM Teflon lid and place it in the rotor of the microwave reactor. 4. Microwave irradiate the mixture for 5 minutes at 300 W power and 80 °C. 5. 5. Upon completion of the reaction, the pH of the reaction mixture was adjusted to 9 with saturated aqueous sodium hydroxide solution. 6. The reaction mixture was extracted twice with dichloroethane. 7. The organic layers were combined and dried with anhydrous sodium sulfate. 8. The solvent was removed by rotary evaporator to give the crude product. 9. The crude product was recrystallized using acetonitrile to give 4.9 g (97% yield) of 2-chloro-N-pyridin-2-ylacetamide as a pink solid. 10. The melting point of the product is 110-115 °C. 11. The product was analyzed by IR (Kjeldahl). 11. The product was analyzed by IR (KBr) and showed characteristic absorption peaks at 3443, 3226, 1683, 1581, 1330, 1198, 775 cm-1. 12. 1H NMR (KBr) analysis showed the product to be in the range of 1H NMR (1H NMR, 1H NMR). 12. 1H NMR (CDCl3) data: δ 4.2 (2H, s), 7.1 (1H, d), 7.7 (1H, t), 8.2 (1H, d, J = 8.3 Hz), 8.4 (1H, d, J = 4.9 Hz), 8.95 (1H, bs). 13. 13C NMR (CDCl3) data: δ 43.2, 111.4, 121.0, 139.1, 148.2, 150.7, 164.9. 14. EIMS analysis showed a molecular ion peak m/z of 170.6 (M+).

References

[1] Patent: US2007/36715, 2007, A1. Location in patent: Page/Page column 4-5
[2] Journal of Enzyme Inhibition and Medicinal Chemistry, 2016, vol. 31, p. 96 - 103
[3] Organic Letters, 2016, vol. 18, # 20, p. 5440 - 5443
[4] Journal of Medicinal Chemistry, 2011, vol. 54, # 7, p. 2060 - 2068
[5] European Journal of Medicinal Chemistry, 2011, vol. 46, # 6, p. 2003 - 2010

2-CHLORO-N-PYRIDIN-2-YL-ACETAMIDE(5221-37-4)Related Product Information

• 2-CHLORO-N-PYRIDIN-2-YL-ACETAMIDE
• 2-CHLORO-N-(5-CHLOROPYRIDIN-2-YL)ACETAMIDE
• N-(5-BROMOPYRIDIN-2-YL)-2-CHLOROACETAMIDE
• 3-CHLORO-1-[3-CHLORO-5-(TRIFLUOROMETHYL)-2-PYRIDINYL]-5-(TRIFLUOROMETHYL)-2(1H)-PYRIDINONE
• 2-CHLORO-N-[3-CHLORO-5-(TRIFLUOROMETHYL)-2-PYRIDINYL]ACETAMIDE
• 2-CHLORO-N-(5-IODO-2-PYRIDINYL)ACETAMIDE
• 4-CHLORO-2-[3-CHLORO-5-(TRIFLUOROMETHYL)-2-PYRIDINYL]-5-PIPERAZINO-3(2H)-PYRIDAZINONE
• 4-CHLORO-2-[3-CHLORO-5-(TRIFLUOROMETHYL)-2-PYRIDINYL]-5-[(2-HYDROXYETHYL)(METHYL)AMINO]-3(2H)-PYRIDAZINONE
• 2-chloro-N-(3-methylpyridin-2-yl)acetamide
• 4-CHLORO-2-[3-CHLORO-5-(TRIFLUOROMETHYL)-2-PYRIDINYL]-5-MORPHOLINO-3(2H)-PYRIDAZINONE
• 4,5-DICHLORO-2-[3-CHLORO-5-(TRIFLUOROMETHYL)-2-PYRIDINYL]-3(2H)-PYRIDAZINONE
• 2-CHLORO-N-(3-[(2,5-DIMETHYLBENZYL)OXY]-6-METHYLPYRIDIN-2-YL)ACETAMIDE
• ETHYL N-[3-(4-(5-CHLORO-1-[3-CHLORO-5-(TRIFLUOROMETHYL)-2-PYRIDINYL]-6-OXO-1,6-DIHYDRO-4-PYRIDAZINYL)PIPERAZINO)-2-CYANOACRYLOYL]CARBAMATE
• 2-CHLORO-4-(2-([3-CHLORO-5-(TRIFLUOROMETHYL)-2-PYRIDINYL]AMINO)ETHYL)PYRIDO[2,3-B]PYRAZIN-3(4H)-ONE
• AKOS BBS-00004071
• 2-CHLORO-N-(4-METHYLPYRIDIN-2-YL)ACETAMIDE
• 2-[(5-CHLORO-1-[3-CHLORO-5-(TRIFLUOROMETHYL)-2-PYRIDINYL]-6-OXO-1,6-DIHYDRO-4-PYRIDAZINYL)(METHYL)AMINO]ETHYL 2,6-DIFLUOROBENZENECARBOXYLATE
• 1-((5-CHLORO-1-[3-CHLORO-5-(TRIFLUOROMETHYL)-2-PYRIDINYL]-6-OXO-1,6-DIHYDRO-4-PYRIDAZINYL)OXY)DIHYDRO-1H-PYRROLE-2,5-DIONE