5-CHLORO-1,2-DIHYDRO-4-METHOXY-2-OXO-3-PYRIDINECARBONITRILE Chemical Properties

Boiling point:

376.8±42.0 °C(Predicted)

Density 

1.43±0.1 g/cm3(Predicted)

storage temp. 

2-8°C

solubility 

Dimethyl Sulfoxide, Methanol

form 

Solid

pka

5.93±0.10(Predicted)

color 

Light Yellow

5-CHLORO-1,2-DIHYDRO-4-METHOXY-2-OXO-3-PYRIDINECARBONITRILE Usage And Synthesis

Chemical Properties

Light Yellow Solid

Uses

3-Cyano Gimeracil Methyl Ether is a useful Intermediate in the synthesis of the antitumor agent Gimeracil.

Uses

Intermediate in the synthesis of antitumor agent Gimeracil.

Synthesis

General procedure for the synthesis of 5-chloro-2-hydroxy-3-cyano-4-methoxypyridine from 4-methoxy-2-oxo-1,2-dihydro-3-cyano-pyridine: 3-cyano-4-methoxy-2(1H)-pyridinone (6.0 g, 0.04 mol) was added to a 250 mL three-necked flask along with 45 mL of glacial acetic acid, and cooled down to below 15 °C. Subsequently, sulfonyl chloride (6.18 g, 0.045 mol) was added slowly, and the temperature of the reaction solution was controlled between 10 and 15 °C, and the titration rate was adjusted according to the temperature change. After the dropwise addition, stirring was continued for 30 min. Then, the reaction mixture was heated to 52 ± 2 °C and the reaction was held at 50-54 °C for 4 hours. The reaction process was monitored by thin layer chromatography (TLC, unfolding agent: ethyl acetate/methanol = 9:1). After confirming the complete reaction of the ingredients, the reaction solution was cooled to 20±2°C and stirred for 2 hours. The solid product was collected by filtration and the filter cake was washed with 58 mL of water. The wet product was dried at 80 °C under atmospheric pressure for 12 h to give 7.01 g of 3-cyano-4-methoxy-5-chloro-2(1H)-pyridinone as a white powder in 95.0% yield (theoretical yield 7.38 g).

References

[1] Patent: CN106316934, 2017, A. Location in patent: Paragraph 0022; 0023; 0025; 0027; 0028
[2] Patent: CN103664772, 2016, B. Location in patent: Paragraph 0013-0017
[3] Heterocycles, 1993, vol. 36, # 1, p. 145 - 148

5-CHLORO-1,2-DIHYDRO-4-METHOXY-2-OXO-3-PYRIDINECARBONITRILE(147619-40-7)Related Product Information

• 5-CHLORO-1,2-DIHYDRO-4-METHOXY-2-OXO-3-PYRIDINECARBONITRILE
• Gimeracil
• 3-Cyano-1,2-dihydro-4-hydroxy-2-oxopyridine
• 4-Methoxy-2-oxo-1,2-dihydro-pyridine-3-carbonitrile