Hydrochloric Acid → 4-(2-Fluoro-5-hydroxy-4-methylanilino)-7-methoxy-6-methoxycarbonylquinoline

HRID 393668ノート

反応式

HRID 393668 の反応式
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:16][CH3:17])=[C:9]([C:12]([O:14][CH3:15])=[O:13])[CH:10]=2)[N:5]=[CH:4][CH:3]=1.[F:18][C:19]1[CH:25]=[C:24]([CH3:26])[C:23]([OH:27])=[CH:22][C:20]=1[NH2:21].Cl>C1(O)CCCCC1.CCOCC>[F:18][C:19]1[CH:25]=[C:24]([CH3:26])[C:23]([OH:27])=[CH:22][C:20]=1[NH:21][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:16][CH3:17])=[C:9]([C:12]([O:14][CH3:15])=[O:13])[CH:10]=2)[N:5]=[CH:4][CH:3]=1

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 101540985-Amino-4-fluoro-2-methylphenolHCID 22646520Methyl 4-chloro-7-methoxyquinoline-6-carboxylate

生成物 1

HCID 226465924-(2-Fluoro-5-hydroxy-4-methylanilino)-7-methoxy-6-methoxycarbonylquinoline

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 7966Cyclohexanol溶媒

反応条件

温度
100 °C

実験手順

A suspension of 4-chloro-7-methoxy-6-methoxycarbonylquinoline (0.252 g, 1 mmol), (prepared as described for the starting material in Example 55), and 2-fluoro-5-hydroxy-4-methylaniline (0.15 g, 1.2 mmol), (prepared as described for the starting material in Example 1), in cyclohexanol (5 ml) containing 1M ethereal hydrogen chloride (1.2 ml) was heated at 100° C. for 2 hours. The mixture was cooled to ambient temperature and diluted with ether. The solid was collected by filtration then absorbed onto silica using methylene chloride/methanol (1/1) containing ammonium hydroxide (1 ml). The product was eluted with methylene chloride/methanol (100/0 increasing to 94:6). Removal of the solvent by evaporation and trituration of the solid with ether followed by collection of the solid by filtration gave 4-(2-fluoro-5-hydroxy-4-methylanilino)-7-methoxy-6-methoxycarbonylquinoline as a cream solid. (195 mg, 54%).

後処理

  1. custom(prepared
  2. custom(prepared
  3. temperatureThe mixture was cooled to ambient temperature
  4. filtrationThe solid was collected by filtration
  5. customthen absorbed onto silica
  6. additioncontaining ammonium hydroxide (1 ml)
  7. washThe product was eluted with methylene chloride/methanol (100/0 increasing to 94:6)
  8. customRemoval of the solvent
  9. customby evaporation and trituration of the solid with ether
  10. filtrationfollowed by collection of the solid by filtration

出典と根拠

ORDレコード
ord-e2e64b1765de4842bfd8fc54795c2460
出典データセット
uspto-grants-2004_10
特許番号
US06809097B1

反応ノート

読み込み中…