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【结 构 式】

【分子编号】33142

【品名】6-nitrobenzo[cd]indol-2(1H)-one

【CA登记号】

【 分 子 式 】C11H6N2O3

【 分 子 量 】214.18032

【元素组成】C 61.69% H 2.82% N 13.08% O 22.41%

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:(VII)

The reaction of 1,8-naphthoic anhydride (I) with hydroxylamine and NaOAc in water gives the N-hydroxynaphthalimide (II), which is condensed with 2,4-dinitrochlorobenzene (III) by means of Na2CO3 in hot water yielding the expected naphthalimide derivative (IV). The rearrangement of (IV) induced by NaOH in ethanol/water affords 8-amino-1-naphthoic acid (V), which is cyclized by means of sulfuric acid to the benz[cd]indolin-2-one (VI). The nitration of (VI) with HNO3 in acetic aid gives the expected 6-nitro derivative (VII), which is reduced with H2 over Pd/C in THF to the corresponding amino derivative (VIII). The condensation of (VIII) with the benzyl bromide (IX) by means of DIEA in hot DMF affords the secondary amine (X), which is methylated with methyl iodide and DIEA in hot DMF to provide the tertiary amine (XI). The reaction of the carbonyl group of (XI) with Lawesson's reagent gives the thione (XII), which is methylated with methyl iodide and NaOH to give the methylsulfanyl derivative (XIII). Finally, this compound is treated with ammonia in methanol.

1 Marzoni, G.; et al.; An improved large-scale synthesis of benz[cd]indol-2(1H)-one and 5-methylbenz[cd]indol-2(1H)-one. Org Process Res Dev 1997, 1, 1, 81.
2 Varney, M.D.; et al.; Crystal-structure-based design and synthesis of benz[cd]indole-containing inhibitors of thymidylate synthase. J Med Chem 1992, 35, 4, 663.
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) 16982 1H,3H-benzo[de]isochromene-1,3-dione; 1,8-Naphthalic Anhydride 81-84-5 C12H6O3 详情 详情
(II) 33138 2-hydroxy-1H-benzo[de]isoquinoline-1,3(2H)-dione 7797-81-1 C12H7NO3 详情 详情
(III) 10378 1-Chloro-2,4-dinitrobenzene 97-00-7 C6H3ClN2O4 详情 详情
(IV) 33139 2-(2,4-dinitrophenoxy)-1H-benzo[de]isoquinoline-1,3(2H)-dione C18H9N3O7 详情 详情
(V) 33140 8-amino-1-naphthoic acid C11H9NO2 详情 详情
(VI) 33141 benzo[cd]indol-2(1H)-one 130-00-7 C11H7NO 详情 详情
(VII) 33142 6-nitrobenzo[cd]indol-2(1H)-one C11H6N2O3 详情 详情
(VIII) 33143 6-aminobenzo[cd]indol-2(1H)-one C11H8N2O 详情 详情
(IX) 33144 4-[[4-(bromomethyl)phenyl]sulfonyl]morpholine C11H14BrNO3S 详情 详情
(X) 33145 6-[[4-(4-morpholinylsulfonyl)benzyl]amino]benzo[cd]indol-2(1H)-one C22H21N3O4S 详情 详情
(XI) 33146 6-[methyl[4-(4-morpholinylsulfonyl)benzyl]amino]benzo[cd]indol-2(1H)-one C23H23N3O4S 详情 详情
(XII) 33147 6-[methyl[4-(4-morpholinylsulfonyl)benzyl]amino]benzo[cd]indole-2(1H)-thione C23H23N3O3S2 详情 详情
(XIII) 33148 N-methyl-2-(methylsulfanyl)-N-[4-(4-morpholinylsulfonyl)benzyl]benzo[cd]indol-6-amine; N-methyl-N-[2-(methylsulfanyl)benzo[cd]indol-6-yl]-N-[4-(4-morpholinylsulfonyl)benzyl]amine C24H25N3O3S2 详情 详情
Extended Information