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

HRID 1648391

반응식

HRID 1648391 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 176Acetic Acid용매

반응 조건

온도
120 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-2102caf230604c98ac327e7a3f369b75
출처 데이터셋
uspto-grants-1995_07
특허 번호
US05436264

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