Ammonium formate → 3-fluoro-4-(2-methyl-1H-imidazol-1-yl)aniline

HRID 723770노트

반응식

HRID 723770 반응식
[F:1][C:2]1[CH:3]=[C:4]([N+:14]([O-])=O)[CH:5]=[CH:6][C:7]=1[N:8]1[CH:12]=[CH:11][N:10]=[C:9]1[CH3:13].C([O-])=O.[NH4+]>CO.O1CCCC1.[Pd]>[NH2:14][C:4]1[CH:5]=[CH:6][C:7]([N:8]2[CH:12]=[CH:11][N:10]=[C:9]2[CH3:13])=[C:2]([F:1])[CH:3]=1

참가 물질

6

반응물 2

HCID 2723923Ammonium formateHCID 218766451-(2-fluoro-4-nitrophenyl)-2-methyl-1H-imidazole

생성물 1

HCID 218766203-fluoro-4-(2-methyl-1H-imidazol-1-yl)aniline수율 100.1%

시약·촉매·용매 3

HCID 23938Palladium촉매HCID 887Methanol용매HCID 8028Tetrahydrofuran용매

실험 절차

3-Fluoro-4-(2-methylimidazol-1-yl)nitrobenzene (40 g, 0.181 M) was dissolved in a mixture of methanol (200 ml) and tetrahydrofuran (800 ml), cooled to 0° under nitrogen, and treated with ammonium formate (57 g, 0.905 M) followed by palladium on charcoal (10%, 2 g). The mixture was stirred at ambient temperature for 18 hours, filtered through celite, celite washed with methanol (100 ml), and filtrate evaporated to dryness. The residue was partitioned between ethyl acetate (800 ml) and 10% aqueous sodium bicarbonate (250 ml). The organic layer was separated, washed with brine (250 ml), dried (magnesium sulfate) and evaporated to give title compound (34.6 g).

후처리

  1. temperaturecooled to 0° under nitrogen
  2. filtrationfiltered through celite, celite
  3. washwashed with methanol (100 ml), and filtrate
  4. customevaporated to dryness
  5. customThe residue was partitioned between ethyl acetate (800 ml) and 10% aqueous sodium bicarbonate (250 ml)
  6. customThe organic layer was separated
  7. washwashed with brine (250 ml)
  8. dry with materialdried (magnesium sulfate)
  9. customevaporated

출처 및 근거

ORD 기록
ord-136172f2f8a74f21a1819ae17354115a
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07141583B2

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