5-nitroisoquinoline -Drug Synthesis Database

【结构式】

【分子编号】22802

【品名】5-nitroisoquinoline

【CA登记号】607-32-9

【分子式】C₉H₆N₂O₂

【分子量】174.15892

【元素组成】C 62.07% H 3.47% N 16.09% O 18.37%

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：(IV)

Quaternization of 5-aminoisoquinoline (I) in acetone afforded isoquinolinium salt (II), which was reduced with NaBH4 to the tetrahydroisoquinoline (III). Alternatively, 5-nitroisoquinoline (IV) was quaternized to give (V) and subsequently reduced with NaBH4 to afford 2-methyl-5-nitro-1,2,3,4-tetrahydroisoquinoline (VI), which was further reduced to amine (III) by catalytic hydrogenation over Pd/C. Amine (III) was finally coupled with acid chloride (VII) in the presence of Et3N to provide the title benzamide).

参考文献中间体

合成目标

【1】 Harling, J.D.; Thompson, M.; Identification of a series of 1,2,3,4-tetrahydrois. 216th ACS Natl Meet (Aug. 23-27, Boston) 1998, Abst MEDI 099.
【2】 Harling, J.D.; Orlek, B.S.; Thompson, M. (SmithKline Beecham plc); Substd. benzamide derivs. and their use as anticon. EP 0906283; US 6110934; WO 9748683 .

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)	22799	5-isoquinolinylamine; 5-isoquinolinamine	1125-60-6	C₉H₈N₂	详情	详情
(II)	22800	2-methyl-2lambda(5)-isoquinolin-5-ylamine; 2-methyl-2lambda(5)-isoquinolin-5-amine		C₁₀H₁₂N₂	详情	详情
(III)	22801	2-methyl-1,2,3,4-tetrahydro-5-isoquinolinylamine; 2-methyl-1,2,3,4-tetrahydro-5-isoquinolinamine		C₁₀H₁₄N₂	详情	详情
(IV)	22802	5-nitroisoquinoline	607-32-9	C₉H₆N₂O₂	详情	详情
(V)	22803	2-methyl-5-nitro-2lambda(5)-isoquinoline		C₁₀H₁₀N₂O₂	详情	详情
(VI)	22804	2-methyl-5-nitro-1,2,3,4-tetrahydroisoquinoline		C₁₀H₁₂N₂O₂	详情	详情
(VII)	22805	5-chloro-4-isopropoxy-2-methoxybenzoyl chloride		C₁₁H₁₂Cl₂O₃	详情	详情

合成路线2

该中间体在本合成路线中的序号：(I)

Treatment of 5-nitroisoquinoline (I) with hydroxylamine and KOH produced 5-nitro-8-aminoisoquinoline (II). Subsequent hydrogenation of (II) over Pd/C gave diamine (III), which was then oxidized to the dichloroquinone (IV) by means potassium chlorate and concentrated HCl. Finally, displacement of the 7-chloro atom of (IV) with p-anisidine (V) in refluxing EtOH yielded the title compound.

参考文献中间体

合成目标

【1】 Ryu, C.-K.; Jung, S.-H.; Lee, C.-O.; Lee, I.-K.; Synthesis and cytotoxic activities of 6-chloro-7-arylamino-5,8-isoquinolinediones. Bioorg Med Chem Lett 1999, 9, 8, 1075.
【2】 Ryu, C.-K.; Jung, S.-H.; Lee, I.-K.; et al.; 7-(Substituted-phenyl)amino-5,8-isoquinolinediones: Synthesis and cytotoxic activities on cancer cell lines. Med Chem Res 2000, 10, 1, 40.

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)	22802	5-nitroisoquinoline	607-32-9	C₉H₆N₂O₂	详情	详情
(II)	31302	5-nitro-8-isoquinolinylamine; 5-nitro-8-isoquinolinamine		C₉H₇N₃O₂	详情	详情
(III)	31303	5,8-isoquinolinediamine; 5-amino-8-isoquinolinylamine		C₉H₉N₃	详情	详情
(IV)	31304	6,7-dichloro-5,8-isoquinolinedione		C₉H₃Cl₂NO₂	详情	详情
(V)	10478	p-Anisidine; 4-Methoxyaniline; 4-Methoxyphenylamine	104-94-9	C₇H₉NO	详情	详情

Extended Information