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

HRID 729269ノート

反応式

HRID 729269 の反応式
[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

参加物

6

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 23925Iron触媒HCID 702Ethanol溶媒HCID 962Water溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-6e2ca894c03e4085a87d43753bd61737
出典データセット
uspto-grants-2009_09
特許番号
US07582629B2

反応ノート

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