2-Nitropropane → 3-(2,2-dimethyl-2-nitroethyl)-5-chloro-1H-indole

HRID 1648391

反応式

HRID 1648391 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11]N(C)C.[OH-].[Na+].[N+:17]([CH:20]([CH3:22])[CH3:21])([O-:19])=[O:18]>C(O)(=O)C>[CH3:21][C:20]([CH3:22])([N+:17]([O-:19])=[O:18])[CH2:11][C:5]1[C:4]2[C:8](=[CH:9][CH:10]=[C:2]([Cl:1])[CH:3]=2)[NH:7][CH:6]=1

参加物

5

反応物 3

HCID 3982-NitropropaneHCID 14798Sodium HydroxideHCID 134914391-(5-Chloro-1H-indol-3-yl)-N,N-dimethylmethanamine

生成物 1

HCID 199199343-(2,2-dimethyl-2-nitroethyl)-5-chloro-1H-indole収率 105.1%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

反応条件

温度
120 °C

実験手順

5-Chloro-3-(dimethylaminomethyl)-1H-indole (10.6 g, 50.5 mmol), prepared as in Example 2, Step (a) and powdered sodium hydroxide (3.0 g, 75.0 mmol) were combined in 2-nitropropane (80 mL, 890.8 mmol) and the mixture was stirred at 120° C. and under nitrogen for 20 hours. The mixture was cooled, acidified with 10% acetic acid (80 mL), stirred at room temperature for 1 hour, and then extracted into ether. The organic phase was separated, washed with water and then brine, dried over magnesium sulfate, and evaporated. Filtration of the residue through a short column of silica gel gave 3-(2,2-dimethyl-2-nitroethyl)-5-chloro-1H-indole (13.5 g, 53.1 mmol) as a yellow oil.

後処理

  1. temperatureThe mixture was cooled
  2. stirringstirred at room temperature for 1 hour
  3. extractionextracted into ether
  4. customThe organic phase was separated
  5. washwashed with water
  6. dry with materialbrine, dried over magnesium sulfate
  7. customevaporated
  8. filtrationFiltration of the residue through a short column of silica gel

出典と根拠

ORDレコード
ord-2102caf230604c98ac327e7a3f369b75
出典データセット
uspto-grants-1995_07
特許番号
US05436264

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