Stannous chloride dihydrate → N-(3-amino-5-bromophenyl)-N-methylacetamide

HRID 1603615노트

반응식

HRID 1603615 반응식
[Br:1][C:2]1[CH:3]=[C:4]([N:11]([CH3:15])[C:12](=[O:14])[CH3:13])[CH:5]=[C:6]([N+:8]([O-])=O)[CH:7]=1.O.O.Cl[Sn]Cl>C(O)C.Cl>[NH2:8][C:6]1[CH:5]=[C:4]([N:11]([CH3:15])[C:12](=[O:14])[CH3:13])[CH:3]=[C:2]([Br:1])[CH:7]=1

참가 물질

5

반응물 2

HCID 61436Stannous chloride dihydrateHCID 10683645N-(3-bromo-5-nitrophenyl)-N-methylacetamide

생성물 1

HCID 10562181N-(3-amino-5-bromophenyl)-N-methylacetamide수율 59%

시약·촉매·용매 2

HCID 313Hydrochloric Acid용매HCID 702Ethanol용매

실험 절차

4.5 g (0.0165 mol) of N-(3-bromo-5-nitrophenyl)-N-methylacetamide were dissolved in 75 ml of ethanol, treated while cooling with a solution of 15.0 g (0.0665 mol) of SnCl2.2H2O in 30 ml of HCl (37%) and stirred at room temperature for 18 hrs. Then, the solvent was removed, the residue was adjusted to pH 8 with sat. NaHCO3 solution, extracted with ethyl acetate and sat. sodium chloride solution and the organic phase was dried over MgSO4, filtered and concentrated. The residue was chromatographed on silica gel with ethyl acetate/hexane 1:2, 1:1 and finally 2:1. There were obtained 2.35 g (59%) of N-(3-amino-5-bromophenyl)-N-methylacetamide as light brown crystals. MS (EI): me/e=244,242 (C9H11BrN2O+).

후처리

  1. additiontreated
  2. customThen, the solvent was removed
  3. extractionextracted with ethyl acetate and sat. sodium chloride solution
  4. dry with materialthe organic phase was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was chromatographed on silica gel with ethyl acetate/hexane 1:2, 1:1 and finally 2:1

출처 및 근거

ORD 기록
ord-579fb267fd4a4ff388122121b7941819
출처 데이터셋
uspto-grants-1999_11
특허 번호
US05990105

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