3-(3-Nitrophenoxy)pyridine → 3-(Pyridin-3-yloxy)aniline

HRID 1696434ノート

反応式

HRID 1696434 の反応式
[N+:1]([C:4]1[CH:5]=[C:6]([CH:14]=[CH:15][CH:16]=1)[O:7][C:8]1[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=1)([O-])=O>CCOC(C)=O.O=[Pt]=O>[N:10]1[CH:11]=[CH:12][CH:13]=[C:8]([O:7][C:6]2[CH:5]=[C:4]([NH2:1])[CH:16]=[CH:15][CH:14]=2)[CH:9]=1

参加物

4

反応物 1

HCID 212855723-(3-Nitrophenoxy)pyridine

生成物 1

HCID 212855823-(Pyridin-3-yloxy)aniline収率 99%

試薬・触媒・溶媒 2

HCID 345198Adams' catalyst触媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 3-(3-nitrophenoxy)pyridine (4.43 g, 20.5 mmol) in EtOAc (50 mL) was added PtO2 (0.4 g) and the mixture was stirred at RT overnight under H2 (1 atm). The mixture was filtered through Celite®, the Celite® washed with EtOAc (2×20 mL) and the combined filtrates concentrated to yield (3.77 g, 99% yield) pure 3-(pyridin-3-yloxy)benzenamine as a syrup. 1H NMR (400 MHz, DMSO-d6): δ 8.34-8.32 (m, 2H), 7.40-7.39 (m, 2H), 7.02 (t, J=8.0 Hz, 1H), 6.37-6.35 (m, 1H), 6.02-6.14 (m, 2H), 5.28 (brs, 2H); MS (ESI) m/z: 187.0 (M+H+).

後処理

  1. filtrationThe mixture was filtered through Celite®
  2. washthe Celite® washed with EtOAc (2×20 mL)
  3. concentrationthe combined filtrates concentrated

出典と根拠

ORDレコード
ord-09377eca088d47899f189386fb06bae7
出典データセット
uspto-grants-2012_04
特許番号
US08163756B2

反応ノート

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