N-(4-fluorophenyl)-2-nitrobenzamide → 2-amino-N-(4-fluorophenyl)benzamide

HRID 427602

反応式

HRID 427602 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:19])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[N+:16]([O-])=O)=[CH:4][CH:3]=1.[BH4-].[Na+]>CO.O1CCCC1.O.O.O.O.C([O-])(=O)C.[Ni+2].C([O-])(=O)C>[NH2:16][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[C:9]([NH:8][C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1)=[O:19]

参加物

6

反応物 2

HCID 691037N-(4-fluorophenyl)-2-nitrobenzamideHCID 4311764Sodium borohydride

生成物 1

HCID 4788222-amino-N-(4-fluorophenyl)benzamide収率 81%

試薬・触媒・溶媒 3

HCID 62601Nickel acetate tetrahydrate触媒HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a stirred solution of N-(4-fluorophenyl)-2-nitrobenzamide (4.0 g, 15.4 mmol) in methanol (220 mL) and tetrahydrofuran (110 mL) was added nickel acetate tetrahydrate (7.7 g, 31 mmol). Sodium borohydride (2.3 g, 62 mmol) was added in small portions. After gas evolution had ceased, the solvent was removed in vacuo. The residue was partitioned between ethyl acetate and concentrated ammonium hydroxide, and the layers were separated. The organic phase was washed with concentrated ammonium hydroxide and saturated aqueous sodium chloride solution, dried (magnesium sulfate), filtered, and concentrated in vacuo to give 2.86 g (81%) of the title compound as an off-white solid.

後処理

  1. customthe solvent was removed in vacuo
  2. customThe residue was partitioned between ethyl acetate and concentrated ammonium hydroxide
  3. customthe layers were separated
  4. washThe organic phase was washed with concentrated ammonium hydroxide and saturated aqueous sodium chloride solution
  5. dry with materialdried (magnesium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-4e3ffc13d5264bc4bc9ada48cfeaba5f
出典データセット
uspto-grants-2001_11
特許番号
US06313122B1

関連ノート

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