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| | 5-CHLORO-1,2-DIHYDRO-4-METHOXY-2-OXO-3-PYRIDINECARBONITRILE Basic information |
| | 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 | Intermediate in the synthesis of antitumor agent Gimeracil. | | Uses | 3-Cyano Gimeracil Methyl Ether is a useful Intermediate in the synthesis of the 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 Preparation Products And Raw materials |
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