2-(4,5-Difluoro-2-nitro-phenyl)-1-(4-methoxy-3-nitro-phenyl)-ethanone → 5-(5,6-difluoro1H-indol-2-yl)-2-methoxy-phenylamine

HRID 25491

反応式

HRID 25491 の反応式
[F:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([CH2:9][C:10]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([N+:20]([O-])=O)[CH:13]=2)=O)=[C:4]([N+:23]([O-])=O)[CH:3]=1>C(O)(=O)C.[Zn]>[F:8][C:7]1[CH:6]=[C:5]2[C:4](=[CH:3][C:2]=1[F:1])[NH:23][C:10]([C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([NH2:20])[CH:13]=1)=[CH:9]2

参加物

4

反応物 1

HCID 225684062-(4,5-Difluoro-2-nitro-phenyl)-1-(4-methoxy-3-nitro-phenyl)-ethanone

生成物 1

HCID 99434395-(5,6-difluoro1H-indol-2-yl)-2-methoxy-phenylamine

試薬・触媒・溶媒 2

HCID 23994Zinc触媒2 回HCID 176Acetic Acid溶媒

実験手順

To a mixture of the product from Step C, 2-(4,5-difluoro-2-nitro-phenyl)-1-(4-methoxy-3-nitro-phenyl)-ethanone (4.00 g, 11.3 mmol) in glacial acetic acid (100 mL) was added in portions zinc dust (28 g, 325 mesh) at 0° C. Upon adding a few portions of zinc, the reaction mixture became a solid mass. The cooling bath was removed, and the remaining zinc was added in portions; the cooling bath was replaced, and stirring was continued for 1 hour at 0° C. and 1 hour at room temperature. The zinc metal was removed by filtration and the metal was washed with ethyl acetate. The organic solution was concentrated to dryness and the residue was partitioned between ethyl acetate (200 mL) and saturated aqueous sodium bicarbonate solution (200 mL). The layers were separated, the organic layer washed with brine, dried (magnesium sulfate), filtered, and concentrated to a tan solid. The solid was triturated with hexanes/ethyl acetate, 15/1, v/v and the insoluble portion collected by filtration (2.35 g), mp 210-211° C.

後処理

  1. customThe cooling bath was removed
  2. additionthe remaining zinc was added in portions
  3. customThe zinc metal was removed by filtration
  4. washthe metal was washed with ethyl acetate
  5. concentrationThe organic solution was concentrated to dryness
  6. customthe residue was partitioned between ethyl acetate (200 mL) and saturated aqueous sodium bicarbonate solution (200 mL)
  7. customThe layers were separated
  8. washthe organic layer washed with brine
  9. dry with materialdried (magnesium sulfate)
  10. filtrationfiltered
  11. concentrationconcentrated to a tan solid
  12. customThe solid was triturated with hexanes/ethyl acetate, 15/1, v/v
  13. filtrationthe insoluble portion collected by filtration (2.35 g), mp 210-211° C.

出典と根拠

ORDレコード
ord-1204068bd25243de98d011573a5f8917
出典データセット
uspto-grants-2005_02
特許番号
US06858739B2

関連ノート

読み込み中…