Hydrazine hydrate (1:1) → 5-Chloro-alpha,alpha-dimethyl-1H-indole-3-ethanamine

HRID 1648392

反応式

HRID 1648392 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][C:12]([CH3:17])([CH3:16])[N+:13]([O-])=O.O.NN>C(O)C.[Ni]>[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][C:12]([NH2:13])([CH3:16])[CH3:17]

参加物

5

反応物 2

HCID 24654Hydrazine hydrate (1:1)HCID 199199343-(2,2-dimethyl-2-nitroethyl)-5-chloro-1H-indole

生成物 1

HCID 132605-Chloro-alpha,alpha-dimethyl-1H-indole-3-ethanamine収率 77%

試薬・触媒・溶媒 2

HCID 935Nickel触媒HCID 702Ethanol溶媒2 回

反応条件

温度
80 °C

実験手順

5-Chloro-3-(2,2-dimethyl-2-nitroethyl)-1H-indole (13.5 g, 53.1 mmol), prepared as in Example 2, Step (b), was dissolved in ethanol (≈100 mL). An aqueous suspension of RANEY NICKEL® catalyst (5.0 mL) was added to the solution and the mixture was heated to 80° C. Hydrazine hydrate (10 mL, 321.1 mmol) in ethanol (≈30 mL) was added dropwise to the mixture which was then stirred for an additional 30 minutes. The mixture was filtered through celite and the filter cake was washed with methanol. The filtrate was concentrated by rotary evaporation to ≈75 mL. Crystallization upon addition of water gave [2-(5-chloro-1H-indol-3-yl)-1,1-dimethylethyl]amine (9.17 g, 40.9 mmol), m.p. 156°-158° C.

後処理

  1. additionwas added to the solution
  2. filtrationThe mixture was filtered through celite
  3. washthe filter cake was washed with methanol
  4. concentrationThe filtrate was concentrated by rotary evaporation to ≈75 mL
  5. customCrystallization
  6. additionupon addition of water

出典と根拠

ORDレコード
ord-752af456e09840168526c78ee15938c1
出典データセット
uspto-grants-1995_07
特許番号
US05436264

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