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ChemicalBook CAS DataBase List 2-Amino-5-fluoropyridine
21717-96-4

2-Amino-5-fluoropyridine synthesis

10synthesis methods
2-Amino-5-fluoropyridine is an important intermediate for the synthesis of LBM415 which is the peptide deformylas inhibitor. Using 2-aminopyridine as raw material and via nitrification, amino acetylation, reduction of nitro, diazolization, Schiemann reaction and hydrolysis of acetyl.
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Yield:21717-96-4 75.5%

Reaction Conditions:

with copper(l) iodide;fluorine;sodium hydroxide in water;1,2-dichloro-ethane at 30 - 40; for 10 h;Inert atmosphere;

Steps:

3 Example 3: Preparation of 2-amino-5-fluoropyridine

Stirring, thermometer, reflux condenser and 20wt% sodium hydroxide aqueous exhaust absorberIn a 500 ml PTFE-lined three-necked flask, 120 g of 1,2-dichloroethane was added.15.8 g (0.2 mol) of 4-cyano-1-butyne, 0.5 g of cuprous chloride (0.005 mol),Under stirring, a nitrogen-diluted fluorine gas (concentration of fluorine gas of 2-5 wt%) is intermittently introduced at 30-35 ° C.A total of 8 grams of fluorine gas was added to the fluorine gas within 5 hours, and then the reaction was stirred at 35-40 ° C for 3 hours.At the same time, the addition reaction was completed by sampling, and then nitrogen gas was bubbled for 2 hours to replace residual fluorine gas and hydrogen fluoride.120 g of 17 wt% aqueous ammonia was added, and the reaction was stirred at 60-65 ° C for 5 hours.Cooled to 20 ° C, layered, and the aqueous layer was extracted three times with 1,2-dichloroethane, 20 g each time.The organic phases were combined and washed with 20 g of saturated brine and dried over 5 g of anhydrous sodium sulfate.The 1,2-dichloroethane was recovered by rotary distillation to obtain 16.9 g of a yellow powder crystal of 2-amino-5-fluoropyridine.The yield was 75.5%, and the gas phase purity was 99.4%.

References:

CN110092746,2019,A Location in patent:Paragraph 0037-0040

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