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

HRID 1296171

Reaktionsgleichung

Reaktionsgleichung von HRID 1296171
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

Komponenten

4

Edukt 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

Produkt 1

HCID 21895285N-[4-[(1E)-3-amino-1-propenyl]phenyl]-4'-(trifluoromethyl)-[1,1'-biphenyl]-2-carboxamideAusbeute 126,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

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.).

Aufarbeitung

  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. washand washed 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

Quellen und Nachweise

ORD-Eintrag
ord-b251f454bb3f4d88a67b8bdc686cc19c
Quelldatensatz
uspto-grants-2007_07
Patentnummer
US07244848B2

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