2-(3-chloro-2-hydroxypropoxy)benzonitrile -Drug Synthesis Database

【结构式】

【分子编号】37570

【品名】2-(3-chloro-2-hydroxypropoxy)benzonitrile

【CA登记号】

【分子式】C₁₀H₁₀ClNO₂

【分子量】211.64764

【元素组成】C 56.75% H 4.76% Cl 16.75% N 6.62% O 15.12%

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：(VIII)

By reaction of 3-(2-methyl-2-aminopropyl)indole (I) and 2-(2,3-epoxypropoxy)benzonitrile (II) by heating at 120-40 C followed by a treatment with HCl in ethanol. The starting products are obtained as follows: 1) The reaction of 3-(dimethylaminomethyl)indole (III) with 2-nitropropane (IV) by means of KOH gives 3-(2-methyl-2-nitropropyl)indole (V), which is then reduced with hydrazine and Raney-Ni in ethanol to yield (I). 2) The reaction of 2-hydroxybenzonitrile (VI) with epichlorohydrin (VII) by means of piperidine affords 2-(3-chloro-2-hydroxypropoxy)benzonitrile (VIII), which is epoxidized again to (II) by treatment with NaOH in hot THF-water.

参考文献中间体

合成目标

【1】 Kreighbaum, W.E.; et al.; Antihypertensive indole derivatives of phenoxypropanolamines with beta-adrenergic receptor antagonist and vasodilating activity. J Med Chem 1980, 23, 3, 285-289.
【2】 Weetman, D.F.; Castaner, J.; Bucindolol Hydrochloride. Drugs Fut 1981, 6, 7, 405.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
	10158	Piperidine	110-89-4	C₅H₁₁N	详情	详情
(I)	37566	2-(1H-indol-3-yl)-1,1-dimethylethylamine; 1-(1H-indol-3-yl)-2-methyl-2-propanamine		C₁₂H₁₆N₂	详情	详情
(II)	37567	2-(2-oxiranylmethoxy)benzonitrile		C₁₀H₉NO₂	详情	详情
(III)	37568	N,N-Dimethyl-1H-indole-3-methanamine;Gramine;N-(1H-indol-3-ylmethyl)-N,N-dimethylamine; 3-(dimethylaminomethyl)-indole[;]1H-indol-3-yl-N,N-dimethylmethanamine	87-52-5	C₁₁H₁₄N₂	详情	详情
(IV)	21819	2-nitropropane	79-46-9	C₃H₇NO₂	详情	详情
(V)	37569	3-(2-methyl-2-nitropropyl)-1H-indole		C₁₂H₁₄N₂O₂	详情	详情
(VI)	21990	2-hydroxybenzonitrile	611-20-1	C₇H₅NO	详情	详情
(VII)	10146	Epichlorohydrin; 2-(Chloromethyl)oxirane	106-89-8	C₃H₅ClO	详情	详情
(VIII)	37570	2-(3-chloro-2-hydroxypropoxy)benzonitrile		C₁₀H₁₀ClNO₂	详情	详情

Extended Information