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

HRID 2041706

반응식

HRID 2041706 반응식
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

참가 물질

5

반응물 2

HCID 2723923Ammonium formate2회HCID 160051694-Methyl-1-(4-nitrophenyl)-1H-imidazole

생성물 1

HCID 160051704-(4-Methyl-1h-imidazol-1-yl)benzenamine수율 90%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 702Ethanol용매

실험 절차

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 of 4-methyl-1-(4-nitrophenyl)-1H-imidazole (for a preparation see intermediate 93) (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.

후처리

  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

출처 및 근거

ORD 기록
ord-caddad1bf5fa4089bbea590acdfd991d
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08580957B2

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