N-phenyl isonicotinamide Chemical Properties

Melting point:

170-172℃

Boiling point:

266℃

Density 

1.227

Flash point:

115℃

storage temp. 

Inert atmosphere,Room Temperature

pka

11.85±0.70(Predicted)

Appearance

White to off-white Solid

Safety Information

HS Code 

29333990

N-phenyl isonicotinamide Usage And Synthesis

Chemical Properties

White to light yellow or grey solid

Synthesis

General procedure for the synthesis of N-phenylisonicotinamide from isonicotinic acid and aniline: isonicotinic acid (14.5 g, 40.6 mmol) was dissolved in thionyl chloride (40 mL) and heated to reflux for 2 hours. After completion of the reaction, thionyl chloride was removed by distillation under reduced pressure. To the residue was added THF (50 mL), K2CO3 (16.8 g, 121.9 mmol) and aniline (3.78 g, 40.6 mmol), and the reaction mixture was stirred at room temperature for 24 hours. After completion of the reaction, the reaction mixture was diluted with water (100 mL) and extracted with EtOAc (2 x 100 mL). The organic layers were combined, concentrated, and the residue was recrystallized with EtOAc-hexane (60:40) to afford the light yellow solid product N-phenylisonicotinamide (8.0 g, 99% yield) with melting point 166-168 °C. IR (KBr) νmax 1344, 1653, 1465, 665 cm-1 ; 1H NMR (DMSO-d6, 300 MHz) δ 10.49 (s, 1H), 8.78 (m, 2H), 7.86 (m, 2H), 7.78 (m, 2H), 7.39 (t, J = 8.0 Hz, 2H), 7.15 (t, J = 6.5 Hz, 1H).

References

[1] Patent: WO2017/160898, 2017, A1. Location in patent: Paragraph 00105; 00125
[2] Journal of Medicinal Chemistry, 2016, vol. 59, # 4, p. 1370 - 1387
[3] Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 11, p. 6027 - 6033
[4] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1981, vol. 20, # 11, p. 1007 - 1008

N-phenyl isonicotinamide(3034-31-9)Related Product Information

• ROQUEFORTINE C
• Isonicotinamide
• Ceramides
• tert-Butyl isonicotinate
• Isonicotinic acid
• Methyl isonicotinate
• ETHYL ISONICOTINOYLACETATE
• METHYL ISONICOTINATE
• Ethyl isonicotinate
• Pyridine-4-carboxylic acid N-oxide
• ANS-NA
• DIPHENYLAMINE HYDROCHLORIDE
• N-O-FLUOROPHENYLGLYCINE
• N-PHENYL-4-BIPHENYLAMINE
• (4-METHOXY-BENZYL)-PHENYL-AMINE
• ISONICOTINOYL CHLORIDE HYDROCHLORIDE
• NICOTINANILIDE
• Inabenfide