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

반응식

HRID 380788 반응식
[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

참가 물질

4

반응물 1

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

생성물 1

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

시약·촉매·용매 2

HCID 23925Iron촉매HCID 176Acetic Acid용매

반응 조건

온도
65 °C

실험 절차

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.).

후처리

  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

출처 및 근거

ORD 기록
ord-e2fd22ce45a94842b667fb8d90cb3450
출처 데이터셋
uspto-grants-2001_10
특허 번호
US06303783B1

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