2-CHLORO-6-METHYLQUINOLINE-3-CARBONITRILE synthesis
- Product Name:2-CHLORO-6-METHYLQUINOLINE-3-CARBONITRILE
- CAS Number:483287-37-2
- Molecular formula:C11H7ClN2
- Molecular Weight:202.64
73568-27-1
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483287-37-2
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Yield:483287-37-2 98%
Reaction Conditions:
Stage #1: 2-chloro-6-methylquinoline-3-carboxaldehydewith hydroxyamino hydrochloride in tetrahydrofuran;lithium hydroxide monohydrate at 20; for 1 h;
Stage #2: with dichlorosulfoxide in chloroform; for 1 h;Reflux;
Steps:
4.3. General procedure for the synthesis of compounds 3a-3f
General procedure: To a solution of hydroxylamine hydrochloride (520 mg,7.5 mmol) in 1mL water, compound 2a-2f (1.65 g, 7.5 mmol) in15 mL THF was added. The reaction mixture was stirred at roomtemperature for 1 h. THF was removed under vacuum. The residuewas stirred in 10 mL water for 10 min. Solid precipitated wasfiltered and dried. The dried solid was dissolved in 15 mL of chloroformand SOCl2 (1.4 mL, 15 mmol) was add slowly to the solution.After refluxing for 1 h, the mixture was concentrated and the residuewas recrystallized with ethanol to give pure product. 1H NMRand 13C NMR data of selected products are shown as follows.
References:
Zhao, Yan;Li, Min;Li, Bowen;Zhang, Shun;Su, Aoze;Xing, Yongning;Ge, Zemei;Li, Runtao;Yang, Baoxue [European Journal of Medicinal Chemistry,2019,vol. 172,p. 131 - 142]
103-89-9
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483287-37-2
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106-49-0
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483287-37-2
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