Hydrazine → N-[4-[(1E)-3-amino-1-propenyl]phenyl]-4'-(trifluoromethyl)-[1,1'-biphenyl]-2-carboxamide

HRID 968917

반응식

HRID 968917 반응식
O=C1C2C(=CC=CC=2)C(=O)[N:3]1[CH2:12]/[CH:13]=[CH:14]/[C:15]1[CH:20]=[CH:19][C:18]([NH:21][C:22]([C:24]2[C:25]([C:30]3[CH:35]=[CH:34][C:33]([C:36]([F:39])([F:38])[F:37])=[CH:32][CH:31]=3)=[CH:26][CH:27]=[CH:28][CH:29]=2)=[O:23])=[CH:17][CH:16]=1.NN>C(O)C>[NH2:3][CH2:12]/[CH:13]=[CH:14]/[C:15]1[CH:20]=[CH:19][C:18]([NH:21][C:22]([C:24]2[C:25]([C:30]3[CH:31]=[CH:32][C:33]([C:36]([F:37])([F:38])[F:39])=[CH:34][CH:35]=3)=[CH:26][CH:27]=[CH:28][CH:29]=2)=[O:23])=[CH:17][CH:16]=1

참가 물질

4

반응물 2

HCID 9321HydrazineHCID 21895288N-[4-[(1E)-3-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-propenyl]phenyl]-4'-(trifluoromethyl)-[1,1'-biphenyl]-2-carboxamide

생성물 1

HCID 21895285N-[4-[(1E)-3-amino-1-propenyl]phenyl]-4'-(trifluoromethyl)-[1,1'-biphenyl]-2-carboxamide수율 126.1%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A mixture of intermediate (2) (0.005 mol) and an aqueous hydrazine solution (0.005 mol) in ethanol (30 ml) was stirred and refluxed for 2 hours. The precipitate was filtered and washed with ethanol. Water was added. The suspension was basified with NaOH and filtered over celite. Celite was washed with ethyl acetate. The filtrate was extracted with ethyl acetate and washed with K2CO3, then with NaCl. The organic layer was separated, dried, filtered, and the solvent was evaporated. The residue was crystallized from ACN. The precipitate was filtered off and dried, yielding 2.5 g of N-[4-[(1E)-3-amino-1-propenyl]phenyl]-4′-(trifluoromethyl)-[1,1′-biphenyl]-2-carboxamide (intermediate 3; mp. 190° C.).

후처리

  1. temperaturerefluxed for 2 hours
  2. filtrationThe precipitate was filtered
  3. washwashed with ethanol
  4. additionWater was added
  5. filtrationfiltered over celite
  6. washCelite was washed with ethyl acetate
  7. extractionThe filtrate was extracted with ethyl acetate
  8. washwashed with K2CO3
  9. customThe organic layer was separated
  10. customdried
  11. filtrationfiltered
  12. customthe solvent was evaporated
  13. customThe residue was crystallized from ACN
  14. filtrationThe precipitate was filtered off
  15. customdried

출처 및 근거

ORD 기록
ord-cb2b59c1e4064a3e9c6569f6b2f322cf
출처 데이터셋
uspto-grants-2007_12
특허 번호
US07304167B2

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