2-Nitro-4-phenylsulfonylphenol → 2-Amino-4-phenylsulfonylphenol

HRID 37104ノート

反応式

HRID 37104 の反応式
[N+:1]([C:4]1[CH:9]=[C:8]([S:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)(=[O:12])=[O:11])[CH:7]=[CH:6][C:5]=1[OH:19])([O-])=O.[H][H]>C(O)C.[Ni]>[NH2:1][C:4]1[CH:9]=[C:8]([S:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)(=[O:12])=[O:11])[CH:7]=[CH:6][C:5]=1[OH:19]

参加物

5

反応物 2

HCID 159333442-Nitro-4-phenylsulfonylphenolHCID 178418361HCID 178418361、化合物

生成物 1

HCID 133660362-Amino-4-phenylsulfonylphenol

試薬・触媒・溶媒 2

HCID 935Nickel触媒HCID 702Ethanol溶媒

実験手順

In 120 ml of dehydrated ethanol was suspended 11.05 g of 2-nitro-4-phenylsulfonylphenol followed by addition of a catalytic amount of Raney nickel for reduction in a hydrogen stream at atmospheric temperature and pressure. After completion of the reduction reaction, the catalyst was filtered off and the solvent was distilled off. The residue was dried under reduced pressure to give 9.73 g-of crude 2-amino-4-phenylsulfonylphenol. This product was dissolved in 19 ml of N,N-dimethylformamide and the solution was added dropwise to a mixture of 5.89 g of potassium fluoride, 7.61 g of ethyl 2-bromoisobutyrate and 11 ml of N,N-dimethylformamide. The mixture was then stirred at 60° C. overnight. The reaction mixture was poured in ice-water and extracted with ethyl acetate. The organic layer was washed with water and dried over anhydrous magnesium sulfate and the solvent was distilled off. The residue was chromatographed on a silica gel column and elution was carried out with hexane-ethyl acetate (2:1). The crude crystals from the eluate were recrystallized from 15 ml of ethanol to recover 4.706 g of 3,4-dihydro-2,2-dimethyl-3-oxo-6-phenylsulfonul-2H-1,4-benzoxazine.

後処理

  1. customAfter completion of the reduction reaction
  2. filtrationthe catalyst was filtered off
  3. distillationthe solvent was distilled off
  4. customThe residue was dried under reduced pressure

出典と根拠

ORDレコード
ord-d56ed43ea56247caa26bf649373bf0f6
出典データセット
uspto-grants-1995_05
特許番号
US05420126

反応ノート

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