2,2-DIMETHYL-N-PYRIDIN-4-YL-PROPIONAMIDE Chemical Properties

Melting point:

73.9-74.0°C

storage temp. 

Inert atmosphere,Room Temperature

solubility 

soluble in Methanol

form 

powder to crystal

color 

White to Almost white

InChI

InChI=1S/C10H14N2O/c1-10(2,3)9(13)12-8-4-6-11-7-5-8/h4-7H,1-3H3,(H,11,12,13)

InChIKey

JCMMVFHXRDNILC-UHFFFAOYSA-N

SMILES

C(NC1C=CN=CC=1)(=O)C(C)(C)C

CAS DataBase Reference

70298-89-4

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

22

HazardClass 

IRRITANT

HS Code 

29333990

2,2-DIMETHYL-N-PYRIDIN-4-YL-PROPIONAMIDE Usage And Synthesis

Chemical Properties

Light yellow solid

Definition

ChEBI: 2,2-Dimethyl-N-(4-pyridinyl)propanamide is a dihydropyridine.

Synthesis

a) General procedure for the synthesis of 2,2-dimethyl-N-(pyridin-4-yl)propionamide: 4-Aminopyridine (2 g, 21.3 mmol) was dissolved in dichloromethane (20 ml), to which pentanoyl chloride (3.1 ml, 25.6 mmol) and triethylamine (8.9 ml, 63.9 mmol) were added sequentially dropwise at room temperature. The reaction mixture was stirred at room temperature for 15 h. The reaction was subsequently quenched by addition of water. The organic layer was extracted with ethyl acetate and the combined organic layers were washed with saturated sodium chloride solution (50 ml), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography with dichloromethane:methanol (20:1, v/v) as eluent. The fraction containing the target product was collected and concentrated to afford N-(pyridin-4-yl)trimethylacetamide as a white solid (3.6 g, 95% yield).1H-NMR (CDCl3, 300 MHz) data were as follows: δ= 8.47 (d, J = 6.1 Hz, 2H), 7.79 (br s, 1H), 7.52 (d, J = 6.0 Hz, 2H), 7.52 (d, J = 6.0 Hz, 2H). 1.32 (s, 9H).

References

[1] Synthesis, 2009, # 13, p. 2267 - 2277
[2] Patent: US2011/28467, 2011, A1. Location in patent: Page/Page column 16
[3] Chemistry - A European Journal, 2013, vol. 19, # 20, p. 6435 - 6442
[4] Molecules, 2003, vol. 8, # 9, p. 678 - 686
[5] European Journal of Medicinal Chemistry, 2005, vol. 40, # 1, p. 15 - 23

2,2-DIMETHYL-N-PYRIDIN-4-YL-PROPIONAMIDE(70298-89-4)Related Product Information

• 4-[(2,2-DIMETHYLPROPANOYL)AMINO]NICOTINIC ACID
• 4-(2,2-DIMETHYL-PROPIONYLAMINO)-NICOTINIC ACID METHYL ESTER
• N-(3-IODO-PYRIDIN-4-YL)-2,2-DIMETHYL-PROPIONAMIDE
• N-(3-FORMYL-4-PYRIDINYL)-2,2-DIMETHYLPROPANAMIDE
• 2,2-DIMETHYL-N-PYRIDIN-4-YL-PROPIONAMIDE
• N-(3-HYDROXY-PYRIDIN-4-YL)-2,2-DIMETHYL-PROPIONAMIDE
• 2,2-DIMETHYL-N-PYRIDIN-2-YL-PROPIONAMIDE
• Propionamide
• (PHENYLCYCLOPENTYL)-N-(4-PYRIDYL)FORMAMIDE
• N-(3-[1,3]DIOXOLAN-2-YL-PYRIDIN-4-YL)-2,2-DIMETHYL-PROPIONAMIDE
• 2,2-DIMETHYL-N-(3-TRIMETHYLSILANYL-PYRIDIN-4-YL)-PROPIONAMIDE
• N-(3-TERT-BUTYLSULFANYL-PYRIDIN-4-YL)-2,2-DIMETHYL-PROPIONAMIDE
• N-(3-DIMETHOXYMETHYL-PYRIDIN-4-YL)-2,2-DIMETHYL-PROPIONAMIDE
• 2,2-DIMETHYL-N-PYRIDIN-3-YL-PROPIONAMIDE
• 3-[4-(2,2-DIMETHYL-PROPIONYLAMINO)-PYRIDIN-3-YL]-ACRYLIC ACID ETHYL ESTER
• RARECHEM AL BI 1299
• RARECHEM AN KA 0922
• N-(2-METHYL(4-QUINOLYL))(PHENYLCYCLOPENTYL)FORMAMIDE