Ammonium Chloride → 1-(5-Amino-1-benzofuran-2-yl)ethanone

HRID 729269

반응식

HRID 729269 반응식
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:11][C:10]([C:12](=[O:14])[CH3:13])=[CH:9][C:8]=2[CH:15]=1)([O-])=O.[NH4+].[Cl-]>CCO.O.[Fe]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]2[O:11][C:10]([C:12](=[O:14])[CH3:13])=[CH:9][C:8]=2[CH:15]=1

참가 물질

6

반응물 2

HCID 25517Ammonium ChlorideHCID 5200231-(5-Nitro-1-benzofuran-2-YL)ethanone

생성물 1

HCID 37833671-(5-Amino-1-benzofuran-2-yl)ethanone수율 54.3%

시약·촉매·용매 3

HCID 23925Iron촉매HCID 702Ethanol용매HCID 962Water용매

실험 절차

Iron powder (0.680 g, 12.19 mmol) was added in portions to a solution of 1-(5-nitro-1-benzofuran-2-yl)ethanone (0.500 g, 2.44 mmol) and NH4Cl (0.652 g, 12.19 mmol) in EtOH (15 mL) and water (4 mL) and the mixture was refluxed for 1 h. The mixture was filtered through Celite and washed out with DCM. The solvents were evaporated and the residue was dissolved in DCM. The organic layer was washed with water, dried through a phase separator and evaporated. The product was purified by silica gel column chromatography using a EtOAc/hexane/MeOH (49:49:2) as eluant, to give the title compound (0.232 g, 54%) as a yellow solid; 1H NMR (500 MHz, CD3OD): δ 7.50 (ds, 1H), 7.33 (d, 1H), 6.95-7.00 (m, 2H), 2.54 (s, 3H); Mass Spectrum: M+H+ 176.

후처리

  1. temperaturethe mixture was refluxed for 1 h
  2. filtrationThe mixture was filtered through Celite
  3. washwashed out with DCM
  4. customThe solvents were evaporated
  5. dissolutionthe residue was dissolved in DCM
  6. washThe organic layer was washed with water
  7. customdried through a phase separator
  8. customevaporated
  9. customThe product was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-6e2ca894c03e4085a87d43753bd61737
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07582629B2

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