N-(4-chloro-2-fluoro-5-nitrophenyl)-3,4,5,6-tetrahydrophthalimide → N-(3-amino-4-chloro-6-fluorophenyl)-3,4,5,6-tetrahydrophthalimide

HRID 380788

反応式

HRID 380788 の反応式
[Cl:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][C:5]([N:11]2[C:20](=[O:21])[C:15]3[CH2:16][CH2:17][CH2:18][CH2:19][C:14]=3[C:12]2=[O:13])=[C:4]([F:22])[CH:3]=1>C(O)(=O)C.[Fe]>[NH2:8][C:7]1[C:2]([Cl:1])=[CH:3][C:4]([F:22])=[C:5]([N:11]2[C:20](=[O:21])[C:15]3[CH2:16][CH2:17][CH2:18][CH2:19][C:14]=3[C:12]2=[O:13])[CH:6]=1

参加物

4

反応物 1

HCID 15590179N-(4-chloro-2-fluoro-5-nitrophenyl)-3,4,5,6-tetrahydrophthalimide

生成物 1

HCID 15590180N-(3-amino-4-chloro-6-fluorophenyl)-3,4,5,6-tetrahydrophthalimide収率 94%

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 176Acetic Acid溶媒

反応条件

温度
65 °C

実験手順

A mixture of N-(4-chloro-2-fluoro-5-nitrophenyl)-1-cyclohexene-1,2-dicarboximide (10.6 g, 32.7 mmol) in acetic acid is heated to 65° C., treated portionwise with iron powder (7.30 g, 130.7 mmol) over 40 minutes, stirred for 10 minutes, and filtered through diatomaceous earth. The resultant filtrate is washed with ethyl acetate, concentrated in vacuo, diluted with ethyl acetate and saturated sodium hydrogen carbonate solution, and filtered through a filter pad. The phases are separated and the organic phase is washed sequentially with saturated sodium hydrogen carbonate solution and brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo to give the title product as a yellow solid (8.94 g, 94% yield, mp 164-165° C.).

後処理

  1. filtrationfiltered through diatomaceous earth
  2. washThe resultant filtrate is washed with ethyl acetate
  3. concentrationconcentrated in vacuo
  4. additiondiluted with ethyl acetate and saturated sodium hydrogen carbonate solution
  5. filtrationfiltered through a filter pad
  6. customThe phases are separated
  7. washthe organic phase is washed sequentially with saturated sodium hydrogen carbonate solution and brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-e2fd22ce45a94842b667fb8d90cb3450
出典データセット
uspto-grants-2001_10
特許番号
US06303783B1

関連ノート

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