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

HRID 850608노트

반응식

HRID 850608 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 23925Iron촉매HCID 962Water용매

실험 절차

To a stirred suspension of 10-2 (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 10-3 which was used without further purification in the next step.

후처리

  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 10-3 which
  9. customwas used without further purification in the next step

출처 및 근거

ORD 기록
ord-530dbc03a8d64c12aa1f8aa740987b75
출처 데이터셋
uspto-grants-2000_01
특허 번호
US06017926

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