METHYL 5-CARBOXY-N-PHENYL-2-1H-PYRIDONE Chemical Properties

Melting point:

160-162 °C

Boiling point:

370.0±42.0 °C(Predicted)

Density 

1.270±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

-1.40±0.63(Predicted)

METHYL 5-CARBOXY-N-PHENYL-2-1H-PYRIDONE Usage And Synthesis

Chemical Properties

White Solid

Uses

A metabolite of Pirfenidone, a new drug to treat patients with kidney disease who have diabetes.

Synthesis

Methyl 6-hydroxynicotinate (6.0 g, 39.22 mmol) and phenylboronic acid (5.74 g, 47.06 mmol) were added copper(II) acetate monohydrate (11.76 g, 58.82 mmol), pyridine (6.32 mL, 78.43 mmol), and molecular sieves (4, 6.0 g) in dichloromethane (100 mL). The reaction mixture was stirred at ambient temperature for 12 h and then filtered. After standard post-extraction treatment the crude product was obtained and purified by silica gel column chromatography (100-200 mesh, eluent chloroform solution containing 1-2% methanol) to afford methyl 6-oxo-1-phenyl-1,6-dihydro-pyridine-3-carboxylate as a brown solid (5.0 g, 56% yield). The product has a melting point of 100-105°C. 1H NMR (400 MHz, CDCl3) δ 3.86 (s, 3H), 6.63 (d, J = 9.5 Hz, 1H), 7.36-7.55 (m, 5H), 7.91 (dd, J = 2.5, 9.9 Hz, 1H), 8.23 (d, J = 2.5 Hz, 1H); IR (KBr ) ν 3058, 2924, 2854, 1721, 1675, 1540, 1446, 1313, 1271, 1103 cm-1; MS 230 (M + 1).

References

[1] Patent: US2008/319026, 2008, A1. Location in patent: Page/Page column 22
[2] Patent: WO2012/122165, 2012, A2. Location in patent: Page/Page column 63

METHYL 5-CARBOXY-N-PHENYL-2-1H-PYRIDONE(77837-09-3)Related Product Information

• 5-CARBOXY-N-PHENYL-2-1H-PYRIDONE
• 1-O-(5-CARBOXY-N-PHENYL-2-1H-PYRIDONE)-D-GLUCURONIC ACID
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