Ammonium formate → 4-(4-Methyl-1h-imidazol-1-yl)benzenamine

HRID 2366892ノート

反応式

HRID 2366892 の反応式
C([O-])=O.[NH4+].[CH3:5][C:6]1[N:7]=[CH:8][N:9]([C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[CH:13][CH:12]=2)[CH:10]=1>C(O)C.[Pd]>[CH3:5][C:6]1[N:7]=[CH:8][N:9]([C:11]2[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][CH:12]=2)[CH:10]=1

参加物

5

反応物 2

HCID 2723923Ammonium formate2 回HCID 160051694-Methyl-1-(4-nitrophenyl)-1H-imidazole

生成物 1

HCID 160051704-(4-Methyl-1h-imidazol-1-yl)benzenamine収率 90.5%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒

実験手順

Ammonium formate (2.202 g, 34.9 mmol) and palladium (10% w/w on carbon, 50% wet, 0.473 g, 4.44 mmol) were added to a solution 4-methyl-1-(4-nitrophenyl)-1H-imidazole (4.73 g, 23.28 mmol) in ethanol (150 mL) and the resulting mixture was refluxed under nitrogen for 1 h then cooled to room temperature. An extra portion of ammonium formate (2.202 g, 34.9 mmol) was then added and the resulting mixture was refluxed for a further hour then cooled to room temperature and filtered through celite. Most of the solvent was removed in vacuo and the residue was loaded on a 50 g SCX column which was eluted with MeOH (5 CV) then with 2N NH3 in MeOH (5 CV). The ammonia fractions were combined and concentrated in vacuo to give 4-(4-methyl-1H-imidazol-1-yl)aniline (3.92 g, 21.06 mmol, 90%) as a yellow solid.

後処理

  1. temperaturethe resulting mixture was refluxed under nitrogen for 1 h
  2. temperaturethe resulting mixture was refluxed for a further hour
  3. temperaturethen cooled to room temperature
  4. filtrationfiltered through celite
  5. customMost of the solvent was removed in vacuo
  6. washwas eluted with MeOH (5 CV)
  7. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-132032d583f441b4ae41e7687144151f
出典データセット
uspto-grants-2014_04
特許番号
US08697725B2

反応ノート

読み込み中…