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

HRID 1603615ノート

反応式

HRID 1603615 の反応式
[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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 313Hydrochloric Acid溶媒HCID 702Ethanol溶媒

実験手順

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+).

後処理

  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

出典と根拠

ORDレコード
ord-579fb267fd4a4ff388122121b7941819
出典データセット
uspto-grants-1999_11
特許番号
US05990105

反応ノート

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