Hydrochloric Acid → methyl (E)-3-(3-aminophenyl)acrylate

HRID 1399939ノート

反応式

HRID 1399939 の反応式
[N+:1]([C:4]1[CH:5]=[C:6](/[CH:10]=[CH:11]/[C:12]([O:14][CH3:15])=[O:13])[CH:7]=[CH:8][CH:9]=1)([O-])=O.Cl>CCO.[Fe]>[NH2:1][C:4]1[CH:5]=[C:6](/[CH:10]=[CH:11]/[C:12]([O:14][CH3:15])=[O:13])[CH:7]=[CH:8][CH:9]=1

参加物

5

反応物 2

HCID 313Hydrochloric AcidHCID 5354136Methyl (2E)-3-(3-nitrophenyl)-2-propenoate

生成物 1

HCID 12394366methyl (E)-3-(3-aminophenyl)acrylate収率 57%

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 702Ethanol溶媒

実験手順

A solution of (E)-methyl 3-(3-nitrophenyl)acrylate (20.14 g, 0.097 mol), Fe (32.5 g, 0.58 mol), concentrated HCl (3.5 ml) in 50% EtOH (100 ml) was refluxed for 2 h. Upon completion, the solution was filtered through Celite and washed with EtOH. The filtrate was concentrated and extracted with dichloromethane. The combined organic phase was dried over MgSO4 and concentrated to afford (E)-methyl 3-(3-aminophenyl)acrylate as a yellow solid (9.73 g, 57%).

後処理

  1. filtrationUpon completion, the solution was filtered through Celite
  2. washwashed with EtOH
  3. concentrationThe filtrate was concentrated
  4. extractionextracted with dichloromethane
  5. dry with materialThe combined organic phase was dried over MgSO4
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-c4c6ac0849a543009493f1c2594735b1
出典データセット
uspto-grants-2014_12
特許番号
US08906909B2

反応ノート

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