4-(methylsulfonyl)-2-nitro-1-[(1E)-prop-1-en-1-yl]benzene → 5-(methylsulfonyl)-2-[(1E)-prop-1-en-1-yl]aniline

HRID 2390156ノート

反応式

HRID 2390156 の反応式
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8](/[CH:11]=[CH:12]/[CH3:13])=[C:7]([N+:14]([O-])=O)[CH:6]=1)(=[O:4])=[O:3]>CC(O)=O.[Fe]>[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8](/[CH:11]=[CH:12]/[CH3:13])=[C:7]([CH:6]=1)[NH2:14])(=[O:3])=[O:4]

参加物

4

反応物 1

HCID 585219844-(methylsulfonyl)-2-nitro-1-[(1E)-prop-1-en-1-yl]benzene2 回

生成物 1

HCID 585220135-(methylsulfonyl)-2-[(1E)-prop-1-en-1-yl]aniline収率 81.4%

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 176Acetic Acid溶媒2 回

反応条件

温度
90 °C

実験手順

A solution of 4-(methylsulfonyl)-2-nitro-1-[(1E)-prop-1-en-1-yl]benzene (Intermediate 59; 1.10 g; 4.56 mmol) in AcOH (7 ml) was treated with powdered iron (3.82 g; 68.4 mmol) and the reaction mixture was stirred at 90° C. for 25 min. Further AcOH was added (20 mL), the solid was filtered off and rinsed with EtOAc. The solvents were removed under reduced pressure, the residue was taken up in EtOAc and washed with saturated NaHCO3 solution twice the with brine. The organic phase was dried on MgSO4, filtered and concentrated under reduced pressure to give the title compound as a brown oil (784 mg, 81%).

後処理

  1. filtrationthe solid was filtered off
  2. washrinsed with EtOAc
  3. customThe solvents were removed under reduced pressure
  4. washwashed with saturated NaHCO3 solution twice the with brine
  5. customThe organic phase was dried on MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-55328cad460c4d87b5cd0170de8399c1
出典データセット
uspto-grants-2012_09
特許番号
US08273769B2

反応ノート

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