5-Methoxy-1H-indole-2,3-dione -Drug Synthesis Database

【结构式】

【分子编号】11892

【品名】5-Methoxy-1H-indole-2,3-dione

【CA登记号】39755-95-8

【分子式】C₉H₇NO₃

【分子量】177.15952

【元素组成】C 61.02% H 3.98% N 7.91% O 27.09%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(V)

This compound can be prepared by two different methods: 1) By cyclocondensation of p-anisidine (I) with 2-oxocyclohexanecarboxylate (II) to 7-methoxy-1,2,3,4-tetrahydroacridone (III), which by treatment with refluxing POCl3 is converted to 9-chloro-7-methoxy-1,2,3,4-tetrahydroacridine (IV). This compound is converted to final product by treatment with NH3 in refluxing p-cresol. 2) By cyclocondensation of 5-methoxyisatin (V) and cyclohexanone (VI) in concentrated aqueous ammonia at 150 C to 7-methoxy-1,2,3,4-tetrahydroacridine-9-carboxamide (VII), followed by a Hoffman degradation with potassium hypobromite.

参考文献中间体

合成目标

【1】 Sigal, M.V. Jr.; Brent, B.J.; Marchini, P.; 7,8,9,10-Tetrahalo-6H-cyclohepta[b]quinolines. US 3232945 .
【2】 Bielavsky, J.; Analogues of 9-amino-1,2,3,4-tetrahydroacridine. Coll Czech Chem Commun 1977, 42, 2802-7.
【3】 Dejmek, L.; 7-MEOTA. Drugs Fut 1990, 15, 2, 126.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
	37678	p-cresol	106-44-5	C₇H₈O	详情	详情
(I)	10478	p-Anisidine; 4-Methoxyaniline; 4-Methoxyphenylamine	104-94-9	C₇H₉NO	详情	详情
(II)	11889	ethyl 2-oxocyclohexanecarboxylate; Ethyl 2-cyclohexanonecarboxylate	1655-07-8	C₉H₁₄O₃	详情	详情
(III)	11890	7-Methoxy-1,3,4,10-tetrahydro-9(2H)-acridinone		C₁₄H₁₅NO₂	详情	详情
(IV)	11891	9-Chloro-5,6,7,8-tetrahydro-2-acridinyl methyl ether; 9-Chloro-7-methoxy-1,2,3,4-tetrahydroacridine		C₁₄H₁₄ClNO	详情	详情
(V)	11892	5-Methoxy-1H-indole-2,3-dione	39755-95-8	C₉H₇NO₃	详情	详情
(VI)	11059	Cyclohexanone	108-94-1	C₆H₁₀O	详情	详情
(VII)	11894	7-Methoxy-1,2,3,4-tetrahydro-9-acridinecarboxamide		C₁₅H₁₆N₂O₂	详情	详情

合成路线2

该中间体在本合成路线中的序号：(I)

The alkaline hydrolysis of 5-methoxyisatin (I) provides the ortho-(aminophenyl)glyoxylic acid salt (II), which is then alkylated by 2-bromoacetophenone (III) to furnish the N-phenacylisatin (IV). Rearrangement of (IV) in the presence of NaOH gives rise to a 40:60 mixture of the indolecarboxylic acid (V) and the target decarboxylated compound.

参考文献中间体

合成目标

【1】 Black, D.S.C.; Wong, L.C.H.; A simple synthesis of 2-acyl indoles from isatins. J Chem Soc Chem Commun 1980, 4, 200.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	11892	5-Methoxy-1H-indole-2,3-dione	39755-95-8	C₉H₇NO₃	详情	详情
(II)	57931	sodium 2-(2-amino-5-methoxyphenyl)-2-oxoacetate		C₉H₈NNaO₄	详情	详情
(III)	10315	2-Bromo-1-phenyl-ethanone; 2-Bromo-1-phenyl-1-ethanone	70-11-1	C₈H₇BrO	详情	详情
(IV)	57932	5-methoxy-1-(2-oxo-2-phenylethyl)-1H-indole-2,3-dione		C₁₇H₁₃NO₄	详情	详情
(V)	57933	2-benzoyl-5-methoxy-1H-indole-3-carboxylic acid		C₁₇H₁₃NO₄	详情	详情

Extended Information