4-phenyl-1,4-dihydrocinnoline -Drug Synthesis Database

【结构式】

【分子编号】37421

【品名】4-phenyl-1,4-dihydrocinnoline

【CA登记号】

【分子式】C₁₄H₁₂N₂

【分子量】208.26276

【元素组成】C 80.74% H 5.81% N 13.45%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号：(I)

The reaction of 1,4-dihydro-4-phenylcinnoline (I) with methyl p-toluenesulfonate (A) and acetic acid by means of KOH in refluxing toluene gives 1-(N-methyl-N-acetylamino)-3-phenylindole (II), which is hydrolyzed by treatment with refluxing concentrated HCl to afford 1-methylamino-3-phenylindole (III). Finally, this compound is condensed with 2-dimethylaminoethyl chloride (IV) by means of sodium amide in refluxing toluene.

参考文献中间体

合成目标

【1】 Schatz, F.; et al.; Amino-3-phenylindoles with antidepressant activity. Binodaline hydrochloride and relatd compounds. Arzneim-Forsch Drug Res 1980, 30, 6, 919-923.
【2】 Schatz, F.; et al. (Siegfried AG); N-Amino indole derivatives having pharmacological activity. US 4204998 .
【3】 Hillier, K.; Castaner, J.; Blancafort, P.; Serradell, M.N.; Binodaline. Drugs Fut 1981, 6, 4, 212.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(A)	23403	Methyl p-toluenesulfonate; Methyl 4-methylbenzenesulfonate; Methyl 4-toluenesulfonate	80-48-8	C₈H₁₀O₃S	详情	详情
(I)	37421	4-phenyl-1,4-dihydrocinnoline		C₁₄H₁₂N₂	详情	详情
(II)	37422	N-methyl-N-(3-phenyl-1H-indol-1-yl)acetamide		C₁₇H₁₆N₂O	详情	详情
(III)	37423	N-methyl-N-(3-phenyl-1H-indol-1-yl)amine; N-methyl-3-phenyl-1H-indol-1-amine		C₁₅H₁₄N₂	详情	详情
(IV)	11907	Dimethylaminoethyl chloride; 2-Dimethylaminoethyl chloride; 2-Chloro-N,N-dimethyl-1-ethanamine; N-(2-Chloroethyl)-N,N-dimethylamine	107-99-3	C₄H₁₀ClN	详情	详情

Extended Information