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

HRID 494158

反応式

HRID 494158 の反応式
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

参加物

4

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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.).

後処理

  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

出典と根拠

ORDレコード
ord-6e274d00fdbe43af8fdd80d9bd1fa93e
出典データセット
uspto-grants-2009_05
特許番号
US07538124B2

関連ノート

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