2-methyl-5-nitro-1,2,3,4-tetrahydroisoquinoline -Drug Synthesis Database

【结构式】

【分子编号】22804

【品名】2-methyl-5-nitro-1,2,3,4-tetrahydroisoquinoline

【CA登记号】

【分子式】C₁₀H₁₂N₂O₂

【分子量】192.21756

【元素组成】C 62.49% H 6.29% N 14.57% O 16.65%

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：(VI)

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

Extended Information