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【结 构 式】

【分子编号】10802

【品名】4-Fluoro-2-(methylamino)benzoic acid

【CA登记号】

【 分 子 式 】C8H8FNO2

【 分 子 量 】169.1554632

【元素组成】C 56.8% H 4.77% F 11.23% N 8.28% O 18.92%

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:(II)

Flosequinan has been synthesized by two new related ways: 1) The reaction of 2-chloro-4-fluorobenzoic acid (I) with refluxing aqueous methylamine Cu powder and CuCl2 gives 4-fluoro-2-(methylamino)benzoic acid (II), which is cyclized with phosgene to yield 7-fluoro-1-methyl-1,2-dihydro-4H-3,1-benzoxazine-2,4-dione (III). The reaction of (III) with dimethyl sulfoxide and NaH in toluene affords 4-fluoro-2-(methylamino)-alpha-(methylsulfinyl)acetophenone (IV), which is finally cyclized with refluxing triethyl orthoformate. 2) The reaction of 2-amino-4-fluorobenzoic acid (V) with phosgene as before gives the corresponding benzoxazine (VI), which is treated with dimethyl sulfoxide and NaH in refluxing toluene to afford 2-amino-4-fluoro-alpha-(methylsulfinyl)acetophenone (VII). The cyclization of (VII) with refluxing trimethyl orthoformate gives 7-fluoro-3-(methylsulfinyl)quinolin-4(1H)-one (VIII), which is finally methylated with dimethyl sulfate and KOH in water.

1 Birch, A.M.; Maclean, L.; Robinson, K.; Davies, R.V.; Syntheses of flosequinan: A novel 4-quinolone shown to be useful in congestive heart failureSyntheses of flosequinan: A novel 4-quinolone shown to be useful in congestive heart failure. J Chem Soc - Perkins Trans I 1994, 4, 387.
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) 10801 2-Chloro-4-fluorobenzoic acid; 4-Fluoro-2-chlorobenzoic acid 2252-51-9 C7H4ClFO2 详情 详情
(II) 10802 4-Fluoro-2-(methylamino)benzoic acid C8H8FNO2 详情 详情
(III) 10803 7-Fluoro-1-methyl-2H-3,1-benzoxazine-2,4(1H)-dione C9H6FNO3 详情 详情
(IV) 10804 1-[4-Fluoro-2-(methylamino)phenyl]-2-(methylsulfinyl)-1-ethanone C10H12FNO2S 详情 详情
(V) 10805 2-Amino-4-fluorobenzoic acid 446-32-2 C7H6FNO2 详情 详情
(VI) 10806 7-Fluoro-2H-3,1-benzoxazine-2,4(1H)-dione C8H4FNO3 详情 详情
(VII) 10807 1-(2-Amino-4-fluorophenyl)-2-(methylsulfinyl)-1-ethanone C9H10FNO2S 详情 详情
(VIII) 10808 7-Fluoro-3-(methylsulfinyl)-4(1H)-quinolinone C10H8FNO2S 详情 详情
Extended Information