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

HRID 1387451노트

반응식

HRID 1387451 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 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.

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 11-3 which
  9. customwas used without further purification in the next step

출처 및 근거

ORD 기록
ord-c1fab15ba21b42e3ab00c763585edd82
출처 데이터셋
uspto-grants-2001_07
특허 번호
US06268378B1

반응 노트

불러오는 중…