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【结 构 式】

【分子编号】62910

【品名】5-Fluoro-4-methoxy-2-nitrophenylamine; 5-Fluoro-4-methoxy-2-nitroaniline

【CA登记号】

【 分 子 式 】C7H7FN2O3

【 分 子 量 】186.1426632

【元素组成】C 45.17% H 3.79% F 10.21% N 15.05% O 25.79%

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:(XLII)

Nitration of 2-fluoroanisole (XXXVII) with HNO3/Ac2O gives 3-fluoro-4-methoxynitrobenzene (XXXVIII), which is reduced to the corresponding aniline (XXXIX) with SnCl2/HCl. Reaction of compound (XXXIX) with Ac2O yields the acetanilide (XL), which is nitrated with HNO3 to afford 5-fluoro-4-methoxy-2-nitroacetanilide (XLI). Hydrolysis of (XLI) with NaOH provides 5-fluoro-4-methoxy-2-nitroaniline (XLII), which is cyclized with buten-2-one (XXXII) by means of As2O5 and H3PO4 to furnish 5-fluoro-6-methoxy-4-methyl-8-nitroquinoline (XLIII). Condensation of quinoline (XLIII) with 3-(trifluoromethyl)phenol (IV) by means of K2CO3 gives the diaryl ether (XXXIV), which is finally reduced by means of H2 over PtO2 in THF.

1 McIntyre, J.A.; Castaner, J.; Bayes, M.; Tafenoquine Succinate. Drugs Fut 2003, 28, 9, 859.
2 LaMontagne, M.P.; Strube, R.E. (Department of the Army); 4-Methyl-5-(unsubstd. and substd. phenoxy)-6-methoxy-8-(aminoalkylamino)quinolines. US 4431807 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(IV) 33504 3-(trifluoromethyl)phenol 98-17-9 C7H5F3O 详情 详情
(XIV) 48075 6-methoxy-4-methyl-5-[3-(trifluoromethyl)phenoxy]-8-quinolinylamine; 6-methoxy-4-methyl-5-[3-(trifluoromethyl)phenoxy]-8-quinolinamine C18H15F3N2O2 详情 详情
(XXXII) 30324 3-buten-2-one; methyl vinyl ketone 78-94-4 C4H6O 详情 详情
(XXXIV) 62906 6-Methoxy-4-methyl-8-nitro-5-[3-(trifluoromethyl)phenoxy]quinoline; 6-Methoxy-4-methyl-8-nitro-5-quinolinyl 3-(trifluoromethyl)phenyl ether C18H13F3N2O4 详情 详情
(XXXVII) 37586 2-fluoroanisole; 1-fluoro-2-methoxybenzene; 2-fluorophenyl methyl ether 321-28-8 C7H7FO 详情 详情
(XXXVIII) 62907 2-Fluoro-4-nitrophenyl methyl ether; 2-Fluoro-1-methoxy-4-nitrobenzene 455-93-6 C7H6FNO3 详情 详情
(XXXIX) 20483 3-fluoro-4-methoxyphenylamine; 3-fluoro-4-methoxyaniline 366-99-4 C7H8FNO 详情 详情
(XL) 62908 N-(3-Fluoro-4-methoxyphenyl)acetamide C9H10FNO2 详情 详情
(XLI) 62909 N-(5-Fluoro-4-methoxy-2-nitrophenyl)acetamide C9H9FN2O4 详情 详情
(XLII) 62910 5-Fluoro-4-methoxy-2-nitrophenylamine; 5-Fluoro-4-methoxy-2-nitroaniline C7H7FN2O3 详情 详情
(XLIII) 62911 5-Fluoro-4-methyl-8-nitro-6-quinolinyl methyl ether; 5-Fluoro-6-methoxy-4-methyl-8-nitroquinoline C11H9FN2O3 详情 详情
Extended Information