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

HRID 1648392

Reaction equation

HRID 1648392 reaction equation
[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]

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent2×

Conditions

Temperature
80 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-752af456e09840168526c78ee15938c1
Source dataset
uspto-grants-1995_07
Patent number
US05436264

Linked notes

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