Cyclohexylamine → 2-Cyclohexylamino-5-nitropyridine

HRID 635008ノート

反応式

HRID 635008 の反応式
[H-].[Na+].[CH:3]1([NH2:9])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.Cl[C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][N:12]=1>O1CCCC1>[CH:3]1([NH:9][C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][N:12]=2)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1

参加物

5

反応物 3

HCID 7965CyclohexylamineHCID 24758Sodium hydrideHCID 783082-Chloro-5-nitropyridine

生成物 1

HCID 2615382-Cyclohexylamino-5-nitropyridine

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
22 °C

実験手順

Sodium hydride (60% dispersion in mineral oil, 1.99 g, 49.8 mmol) was washed 3× with hexanes then a solution of cyclohexylamine (3.8 mL, 33.2 mmol) dissolved in tetrahydrofuran (50 mL) was added. After stirring for 30 minutes at 22° C., 2-chloro-5-nitropyridine (5.00 g, 31.5 mmol) was added and the reaction mixture was heated to reflux for 3 hours. The solution was cooled to ambient temperature, quenched with saturated aqueous NH4Cl and concentrated in vacuo. The residue was redissolved in ethyl acetate then washed 2× with saturated NaHCO3, saturated NaCl, dried over anhydrous Na2SO4 and concentrated in vacuo. The product was recovered as a brown oil.

後処理

  1. additionwas added
  2. temperaturethe reaction mixture was heated
  3. temperatureto reflux for 3 hours
  4. temperatureThe solution was cooled to ambient temperature
  5. customquenched with saturated aqueous NH4Cl
  6. concentrationconcentrated in vacuo
  7. dissolutionThe residue was redissolved in ethyl acetate
  8. washthen washed 2× with saturated NaHCO3, saturated NaCl
  9. dry with materialdried over anhydrous Na2SO4
  10. concentrationconcentrated in vacuo
  11. customThe product was recovered as a brown oil

出典と根拠

ORDレコード
ord-39685aeb810e435ab03d74132aff5799
出典データセット
uspto-grants-2001_02
特許番号
US06184237B2

反応ノート

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