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【结 构 式】

【分子编号】25244

【品名】7-chloro-4a,8a-dihydro-1-quinoliniumolate

【CA登记号】

【 分 子 式 】C9H8ClNO

【 分 子 量 】181.62136

【元素组成】C 59.52% H 4.44% Cl 19.52% N 7.71% O 8.81%

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 acetylation of 3-chloroaniline (I) with refluxing acetic anhydride gives the corresponding anilide (II), which is nitrated with HNO3/H2SO4 yielding 5-chloro-2-nitroacetanilide (III). The hydrolysis of (III) with hot conc. H2SO4 affords 5-chloro-2-nitroaniline (IV), which is treated with NaNO2/HCl to afford the corresponding diazonium salt (V). The reaction of (V) with sodium azide gives 2-nitro-5-chlorophenylazide (VI), which is cyclized to 5-chlorobenzofurazan-3-oxide (VII) in refluxing toluene. The condensation of (VII) with malononitrile (VIII) in DMF in the presence of a catalytic amount of triethylamine afforded a mixture of the isomeric quinoxaline-di-N-oxides (IX and X), which were separated by flash chromatography. The 7-chloro isomer (XI) was then submitted to diazotization with tert-butyl nitrite in acetonitrile in the presence of cupric chloride, which effected a Sandmeyer reaction to give the 2,6-dichloro derivative (XI). N-Alkylation of 3-(N,N-dimethylamino)propylamine (XII) with intermediate (XI) in dichloromethane in the presence of potassium carbonate, followed by treatment with concentrated hydrochloric acid in acetone afforded the title compound.

1 Monge, A.; et al.; Hypoxia-selective agents derived from quinoxaline 1, 4-di-N-oxides. J Med Chem 1995, 38, 10, 1786.
2 Monge, A.; et al.; Hypoxia-selective agents derived from 2-quinoxalinecarbonitrile 1,4-di-N-oxides. 2. J Med Chem 1995, 38, 22, 4488.
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) 25239 3-chloroaniline; 3-chlorophenylamine 108-42-9 C6H6ClN 详情 详情
(II) 25240 N-(3-chlorophenyl)acetamide 588-07-8 C8H8ClNO 详情 详情
(III) 25241 N-(5-chloro-2-nitrophenyl)acetamide 39163-92-3 C8H7ClN2O3 详情 详情
(IV) 15709 5-chloro-2-nitrophenylamine; 5-chloro-2-nitroaniline 1635-61-6 C6H5ClN2O2 详情 详情
(V) 25242 5-chloro-2-nitrobenzenediazonium chloride 2589-71-1 C6H3Cl2N3O2 详情 详情
(VI) 25243 2-azido-4-chloro-1-nitrobenzene C6H3ClN4O2 详情 详情
(VII) 25244 7-chloro-4a,8a-dihydro-1-quinoliniumolate C9H8ClNO 详情 详情
(VIII) 12061 Malononitrile 109-77-3 C3H2N2 详情 详情
(IX) 25245 2-amino-6-chloro-3-cyano-1,4-quinoxalinediiumdiolate C9H5ClN4O2 详情 详情
(X) 25246 3-amino-6-chloro-2-cyano-1,4-quinoxalinediiumdiolate C9H5ClN4O2 详情 详情
(XI) 25247 2,6-dichloro-3-cyano-1,4-quinoxalinediiumdiolate C9H3Cl2N3O2 详情 详情
(XII) 25248 N-(3-aminopropyl)-N,N-dimethylamine; N(1),N(1)-dimethyl-1,3-propanediamine 109-55-7 C5H14N2 详情 详情
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