Acetic Acid → N2-[4-(benzyloxy)phenyl]-4-methylpyridine-2,3-diamine

HRID 572187ノート

反応式

HRID 572187 の反応式
C(O)(=O)C.[CH2:5]([O:12][C:13]1[CH:18]=[CH:17][C:16]([NH:19][C:20]2[C:25]([N+:26]([O-])=O)=[C:24]([CH3:29])[CH:23]=[CH:22][N:21]=2)=[CH:15][CH:14]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>C1COCC1.[Zn]>[CH2:5]([O:12][C:13]1[CH:18]=[CH:17][C:16]([NH:19][C:20]2[C:25]([NH2:26])=[C:24]([CH3:29])[CH:23]=[CH:22][N:21]=2)=[CH:15][CH:14]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

参加物

5

反応物 2

HCID 176Acetic AcidHCID 58577297N-[4-(benzyloxy)phenyl]-4-methyl-3-nitropyridin-2-amine

生成物 1

HCID 58577506N2-[4-(benzyloxy)phenyl]-4-methylpyridine-2,3-diamine収率 70%

試薬・触媒・溶媒 2

HCID 23994Zinc触媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a mixture of zinc (40.2 g), THF (50 ml) and acetic acid (100 ml) was added slowly a solution of N-[4-(benzyloxy)phenyl]-4-methyl-3-nitropyridin-2-amine (13.75 g) in THF (150 ml), and the obtained mixture was stirred at room temperature for 30 min. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure. The residue was diluted with ethyl acetate, washed with 1 M aqueous sodium hydroxide solution and saturated brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by basic silica gel column chromatography (hexane/ethyl acetate) and recrystallized from hexane/ethyl acetate to give the title compound (8.77 g).

後処理

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. additionThe residue was diluted with ethyl acetate
  4. washwashed with 1 M aqueous sodium hydroxide solution and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by basic silica gel column chromatography (hexane/ethyl acetate)
  8. customrecrystallized from hexane/ethyl acetate

出典と根拠

ORDレコード
ord-5255e91a25ce4e91b1675ac650228100
出典データセット
uspto-grants-2015_05
特許番号
US09029388B2

反応ノート

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