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

HRID 1648392

반응식

HRID 1648392 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][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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 935Nickel촉매HCID 702Ethanol용매2회

반응 조건

온도
80 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-752af456e09840168526c78ee15938c1
출처 데이터셋
uspto-grants-1995_07
특허 번호
US05436264

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