Water → (6-Methyl-3-nitro-2-phenoxypyridin-4-yl)-{2-[3-(pyridin-3-yl)propoxy]ethyl}amine

HRID 1008052ノート

反応式

HRID 1008052 の反応式
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Cl[C:11]1[C:16]([N+:17]([O-:19])=[O:18])=[C:15]([NH:20][CH2:21][CH2:22][O:23][CH2:24][CH2:25][CH2:26][C:27]2[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=2)[CH:14]=[C:13]([CH3:33])[N:12]=1.O>COCCOCCOC>[CH3:33][C:13]1[N:12]=[C:11]([O:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:16]([N+:17]([O-:19])=[O:18])=[C:15]([NH:20][CH2:21][CH2:22][O:23][CH2:24][CH2:25][CH2:26][C:27]2[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=2)[CH:14]=1

参加物

6

反応物 4

HCID 962WaterHCID 996Phenol2 回HCID 24758Sodium hydride2 回HCID 21913307(2-Chloro-6-methyl-3-nitropyridin-4-yl)-{2-[3-(pyridin-3-yl)propoxy]ethyl}amine

生成物 1

HCID 21913338(6-Methyl-3-nitro-2-phenoxypyridin-4-yl)-{2-[3-(pyridin-3-yl)propoxy]ethyl}amine収率 129.4%

試薬・触媒・溶媒 1

HCID 8150Diglyme溶媒3 回

反応条件

温度
60 °C

実験手順

The general method described in Part E of Example 80 was used with the following modifications. A solution of phenol (1.45 g, 15.4 mmol) in diglyme (10 mL) was added to a cooled mixture of the sodium hydride dispersion (0.59 g, 14.7 mmol) in diglyme (15 mL), and the addition flask was rinsed twice with diglyme (5 mL), which was added to the reaction. A solution of (2-chloro-6-methyl-3-nitropyridin-4-yl)-{2-[3-(pyridin-3-yl)propoxy]ethyl}amine (4.9 g, 14 mmol) was added, and the reaction was heated at 60° C. for 20 hours. Additional reagent prepared from phenol (0.50 g, 5.3 mmol) and 60% sodium hydride (0.21 g, 5.3 mmol) in diglyme was added, and the reaction was heated at 60° C. for 2.5 hours. The reaction was allowed to cool to room temperature and slowly added to 800 mL of water and stirred for one hour to form a bright yellow solid. The solid was isolated by filtration and washed with hexane (50 mL) to provide 7.4 g of (6-methyl-3-nitro-2-phenoxypyridin-4-yl)-{2-[3-(pyridin-3-yl)propoxy]ethyl}amine as a yellow solid contaminated with water.

後処理

  1. washthe addition flask was rinsed twice with diglyme (5 mL), which
  2. additionwas added to the reaction
  3. additionwas added
  4. temperaturethe reaction was heated at 60° C. for 2.5 hours
  5. temperatureto cool to room temperature
  6. customto form a bright yellow solid
  7. customThe solid was isolated by filtration
  8. washwashed with hexane (50 mL)

出典と根拠

ORDレコード
ord-a7e4e85a90454800b93629816a274efc
出典データセット
uspto-grants-2004_09
特許番号
US06797718B2

反応ノート

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