Ethanol → 3-(4-Amino-3-hydroxyphenyl)-acrylic acid ethyl ester

HRID 1108402ノート

反応式

HRID 1108402 の反応式
[CH2:1]([O:3][C:4](=[O:17])[CH:5]=[CH:6][C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[C:9]([OH:16])[CH:8]=1)[CH3:2].[NH4+].[Cl-].CCO>[Fe].O>[CH2:1]([O:3][C:4](=[O:17])[CH:5]=[CH:6][C:7]1[CH:12]=[CH:11][C:10]([NH2:13])=[C:9]([OH:16])[CH:8]=1)[CH3:2]

参加物

6

反応物 3

HCID 702EthanolHCID 25517Ammonium ChlorideHCID 54189784Ethyl 3-hydroxy-4-nitrocinnamate

生成物 1

HCID 540473973-(4-Amino-3-hydroxyphenyl)-acrylic acid ethyl ester

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 962Water溶媒

実験手順

To a stirred suspension of 11-2 (4.64 g, 19.6 mmol), NH4Cl (524 mg, 9.8 mmol), EtOH (140 mL) and H2O (70 mL) was added iron dust (2.72 g, 48.9 mmol). The resulting yellow suspension was refluxed for 1.5 h., and then the solution was filtered while hot through celite. The filtrate was concentrated and the residue was partitioned between EtOAc and brine. The layers were separated and the EtOAc layer dried (Na2SO4) and concentrated to give 11-3 which was used without further purification in the next step.

後処理

  1. temperatureThe resulting yellow suspension was refluxed for 1.5 h.
  2. filtrationthe solution was filtered while hot through celite
  3. concentrationThe filtrate was concentrated
  4. customthe residue was partitioned between EtOAc and brine
  5. customThe layers were separated
  6. dry with materialthe EtOAc layer dried (Na2SO4)
  7. concentrationconcentrated
  8. customto give 11-3 which
  9. customwas used without further purification in the next step

出典と根拠

ORDレコード
ord-2649e4909ed3444b87b1e6d3622b382d
出典データセット
uspto-grants-2000_05
特許番号
US06066648

反応ノート

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