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

HRID 37104노트

반응식

HRID 37104 반응식
[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]

참가 물질

5

반응물 2

HCID 159333442-Nitro-4-phenylsulfonylphenolHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 133660362-Amino-4-phenylsulfonylphenol

시약·촉매·용매 2

HCID 935Nickel촉매HCID 702Ethanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-d56ed43ea56247caa26bf649373bf0f6
출처 데이터셋
uspto-grants-1995_05
특허 번호
US05420126

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