5-CARBOXY-N-PHENYL-2-1H-PYRIDONE

5-CARBOXY-N-PHENYL-2-1H-PYRIDONE Property

Melting point:

282-284°C

storage temp. 

Sealed in dry,Room Temperature

solubility 

DMSO (Slightly), Methanol (Slightly)

form 

Solid

color 

Off-White to Light Yellow

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P321Specific treatment (see … on this label).

P330Rinse mouth.

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

P501Dispose of contents/container to..…

5-CARBOXY-N-PHENYL-2-1H-PYRIDONE Chemical Properties,Usage,Production

Chemical Properties

Off-White Fluffy Solid

Uses

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

Synthesis

General procedure for the synthesis of 6-oxo-1-phenyl-1,6-dihydro-pyridine-3-carboxylic acid from methyl 6-oxo-1-phenyl-1,6-dihydro-pyridine-3-carboxylate: at 0 °C, lithium hydroxide monohydrate (0.366 g, 8.73 mmol) was added to a mixed solution of tetrahydrofuran (9 mL) and water (6 mL) containing methyl 6-oxo-1-phenyl-1,6-dihydropyridine-3-carboxylate (1.0 g, 4.37 mmol) in a mixed solution of tetrahydrofuran (9 mL) and water (6 mL) and the reaction was stirred for 1 hour. After completion of the reaction, the reaction mixture was diluted with water and washed with ethyl acetate. Subsequently, the pH of the aqueous layer was adjusted to 2 with 2N hydrochloric acid and the precipitate was collected by filtration to afford 6-oxo-1-phenyl-1,6-dihydropyridine-3-carboxylic acid as a brown solid (0.740 g, 79% yield). The melting point of the product was 256-263°C. The structure of the product was determined by 1H NMR (400 MHz, DMSO-d6) δ 6.53 (d, J = 9.4 Hz, 1H), 7.40-7.49 (m, 5H), 7.87 (dd, J = 2.5, 9.8 Hz, 1H), 8.23 (d, J = 2.5 Hz, 1H); IR (KBr) ν 3446, 1708, 1645, 1577, 1263, 1228 cm-1; MS 214 (M-1) for characterization.

References

[1] Archiv der Pharmazie, 2013, vol. 346, # 9, p. 654 - 666
[2] Patent: US2008/319026, 2008, A1. Location in patent: Page/Page column 22
[3] Patent: WO2012/122165, 2012, A2. Location in patent: Page/Page column 63-64
[4] Patent: US2013/317059, 2013, A1. Location in patent: Paragraph 0042-0043
[5] Journal of Medicinal Chemistry, 2013, vol. 56, # 12, p. 5079 - 5093