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

HRID 1167488ノート

反応式

HRID 1167488 の反応式
[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]=[C:11]([CH3:13])[N:10]=[CH:9]1.C([O-])=O.[NH4+]>CO.O1CCCC1.[Pd]>[NH2:14][C:4]1[CH:5]=[CH:6][C:7]([N:8]2[CH:12]=[C:11]([CH3:13])[N:10]=[CH:9]2)=[C:2]([F:1])[CH:3]=1

参加物

6

反応物 2

HCID 2723923Ammonium formateHCID 218765961-(2-fluoro-4-nitrophenyl)-4-methyl-1H-imidazole

生成物 1

HCID 218766383-Fluoro-4-(4-methyl-1H-imidazol-1-yl)aniline収率 90.5%

試薬・触媒・溶媒 3

HCID 23938Palladium触媒HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

3-Fluoro4-(4-methyl-imidazol-1-yl)nitrobenzene (64.7 g, 0.293 M) was dissolved in a mixture of MeOH (200 ml) and tetrahydrofuran (800 ml), cooled to 0° under nitrogen, and treated with ammonium formate (99.3 g, 1.46 M) followed by palladium on charcoal (10%. 2.5 g). The mixture was stirred at ambient temperature for 48 hours, filtered through celite, celite washed with MeOH (200 ml), and filtrate evaporated to dryness. The residue was partitioned between EtOAc (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 (50.6 g).

後処理

  1. temperaturecooled to 0° under nitrogen
  2. filtrationfiltered through celite, celite
  3. washwashed with MeOH (200 ml), and filtrate
  4. customevaporated to dryness
  5. customThe residue was partitioned between EtOAc (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

出典と根拠

ORDレコード
ord-4fe3fbdddf794d7ba7c0bca1f7ba7191
出典データセット
uspto-grants-2003_09
特許番号
US06617339B1

反応ノート

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