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【结 构 式】

【分子编号】41150

【品名】6-nitro-1,2,3,4-tetrahydroisoquinoline

【CA登记号】

【 分 子 式 】C9H10N2O2

【 分 子 量 】178.19068

【元素组成】C 60.66% H 5.66% N 15.72% O 17.96%

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:(XVIII)

Condensation of 2-chloro-4-nitrobenzoic acid (XII) with dimethyl malonate produced the arylmalonate (XIII). Hydrolysis and subsequent decarboxylation of (XIII) afforded diacid (XIV). This was converted into cyclic anhydride (XV) upon refluxing with Ac2O and then reduced to diol (XVI) with borane in THF. Optionally, diol (XVI) was obtained by direct reduction of diacid (XIV) with borane. After conversion of (XVI) to dimesylate (XVII), cyclization with ammonia produced tetrahydroisoquinoline (XVIII). This was protected as the N-Boc derivative (XIX) and the nitro group was reduced to the target amine (VII) by hydrogenation over Pt/C .

1 Quallich, G.J.; Dorff, P.H.; Chang, G. (Pfizer Inc.); Biphenyl-2-carboxylic acid-tetrahydro-isoquinolin-6-yl amide derivs., their preparation and their use as inhibitors of microsomal triglyceride transfer protein and/or apolipoprotein B (Apo B) secretion. JP 1999514964; US 5919795; WO 9640640 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(VII) 41145 tert-butyl 6-amino-3,4-dihydro-2(1H)-isoquinolinecarboxylate C14H20N2O2 详情 详情
(XII) 41126 2-chloro-4-nitrobenzoic acid 99-60-5 C7H4ClNO4 详情 详情
(XIII) 41127 2-[2-methoxy-1-(methoxycarbonyl)-2-oxoethyl]-4-nitrobenzoic acid C12H11NO8 详情 详情
(XIV) 41128 2-(carboxymethyl)-4-nitrobenzoic acid C9H7NO6 详情 详情
(XV) 41129 6-nitro-1H-isochromene-1,3(4H)-dione C9H5NO5 详情 详情
(XVI) 41130 2-[2-(hydroxymethyl)-5-nitrophenyl]-1-ethanol C9H11NO4 详情 详情
(XVII) 41149 2-[[(methylsulfonyl)oxy]methyl]-5-nitrophenethyl methanesulfonate C11H15NO8S2 详情 详情
(XVIII) 41150 6-nitro-1,2,3,4-tetrahydroisoquinoline C9H10N2O2 详情 详情
(XIX) 41151 tert-butyl 6-nitro-3,4-dihydro-2(1H)-isoquinolinecarboxylate C14H18N2O4 详情 详情
Extended Information