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【结 构 式】

【分子编号】50326

【品名】2-Bromo-5-methoxyaniline

【CA登记号】129968-11-2

【 分 子 式 】C7H8BrNO

【 分 子 量 】202.05066

【元素组成】C 41.61% H 3.99% Br 39.55% N 6.93% O 7.92%

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:(XI)

The alkylation of 4-hydroxy-3-methoxybenzoic acid methyl ester (I) with 3-(4-morpholinyl)propyl chloride (II) and tetrabutylammonium chloride in refluxing butanone gives 3-methoxy-4-[3-(4-morpholinyl)propoxy]benzoic acid methyl ester (III), which is nitrated with HNO3 in hot acetic acid to yield 5-methoxy-4-[3-(4-morpholinyl)propoxy]-2-nitrobenzoic acid methyl ester (IV). The reduction of (III) with H2 over Pd/C in methanol/ethyl acetate to afford the corresponding 2-amino ester (V), which is condensed with dimethylformamide dimethylacetal (VI) by heating at 100 C to provide the 2-(dimethylaminomethyleneamino) derivative (VII). The cyclization of (VII) with acetonitrile (VIII) by means of BuLi and CO2 in THF gives 6-methoxy-7-[3-(4-morpholinyl)propoxy]-4-oxo-1,4-dihydroquinoline-3-carbonitrile (IX), which is treated with refluxing SOCl2 to yield the 4-chloroquinoline derivative (X). Finally, this compound is condensed with 2-bromo-5-methoxyaniline by means of pyridine hydrochloride in 2-ethoxyethanol or NaH in THF (or DMF).

1 Wang, Y.D.; et al.; Inhibition of SRC kinase activity by 4-phenylamino-3-quinolinecarbonitriles, Part 1: optimization of the aniline headpiece at C-4. 221st ACS Natl Meet (April 1 2001, San Diego) 2001, Abst MEDI 144.
2 Tsou, H.-R.; Wissner, A.; Johnson, B.D.; Reich, M.F.; Floyd, M.B. Jr.; Kitchen, D.B. (American Cyanamid Co.); Substituted 3-cyano quinolines. US 6002008 .
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) 29176 methyl 4-hydroxy-3-methoxybenzoate 3943-74-6 C9H10O4 详情 详情
(II) 18691 4-(3-chloropropyl)morpholine;N-(3-Chloropropyl)morpholine 7357-67-7 C7H14ClNO 详情 详情
(III) 50321 methyl 3-methoxy-4-[3-(4-morpholinyl)propoxy]benzoate C16H23NO5 详情 详情
(IV) 50322 methyl 5-methoxy-4-[3-(4-morpholinyl)propoxy]-2-nitrobenzoate C16H22N2O7 详情 详情
(V) 50323 methyl 2-amino-5-methoxy-4-[3-(4-morpholinyl)propoxy]benzoate C16H24N2O5 详情 详情
(VI) 11984 N-(Dimethoxymethyl)-N,N-dimethylamine;dimethylformamide dimethylacetal;1,1-dimethoxy-N,N-dimethylmethanamine; Dimethoxy-N,N-dimethylmethanamine; N,N-Dimethylformamide dimethyl acetal 4637-24-5 C5H13NO2 详情 详情
(VII) 50324 methyl 2-[[(E)-(dimethylamino)methylidene]amino]-5-methoxy-4-[3-(4-morpholinyl)propoxy]benzoate C19H29N3O5 详情 详情
(VIII) 50327 Cyanoethane; Ethyl cyanide; Propionitrile 107-12-0 C26H39NO5 详情 详情
(IX) 50325 6-methoxy-7-[3-(4-morpholinyl)propoxy]-4-oxo-1,4-dihydro-3-quinolinecarbonitrile C18H21N3O4 详情 详情
(X) 48517 4-chloro-6-methoxy-7-[3-(4-morpholinyl)propoxy]-3-quinolinecarbonitrile C18H20ClN3O3 详情 详情
(XI) 50326 2-Bromo-5-methoxyaniline 129968-11-2 C7H8BrNO 详情 详情
Extended Information