Ethyl Acetate → HCID 43165373, compound

HRID 2245501Notes

Reaction equation

HRID 2245501 reaction equation
[C:1]([C:5]1[CH:23]=[CH:22][C:8]([CH2:9][N:10]2[C:18]3[C:13](=[CH:14][C:15]([N+:19]([O-])=O)=[CH:16][CH:17]=3)[CH:12]=[CH:11]2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].NN.CCOC(C)=O>CCO.O.[Ni]>[C:1]([C:5]1[CH:23]=[CH:22][C:8]([CH2:9][N:10]2[C:18]3[C:13](=[CH:14][C:15]([NH2:19])=[CH:16][CH:17]=3)[CH:12]=[CH:11]2)=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 3

HCID 8857Ethyl AcetateHCID 9321HydrazineHCID 68541311HCID 68541311, compound

Product 1

HCID 43165373HCID 43165373, compoundYield 96.5%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
45 °C

Procedure

To 1-(4-tert-butylbenzyl)-5-nitro-1H-indole (1.00 g, 3.24 mmol) in EtOH (35 ml) at ambient temperature under a nitrogen atmosphere was added hydrazine (2.0 g, 62.5 mmol) and Raney-Ni (0.20 g of a 50% slurry in H2O). The yellow mixture was stirred at 45° C. for 1 hr. The mixture was cooled to room temperature and filtered through a celite pad (1×4.25 cm). The pad was washed with EtOH (10 ml) and concentrated in vacuo to afford a dark yellow powder. Gradient SiO2 chromatography (Hex:EtOAc) afforded 1-(4-tert-butylbenzyl)-5-amino-1H-indole as a yellow powder (0.87 g, 96% yield): MS (ESI) m/z 279.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. filtrationfiltered through a celite pad (1×4.25 cm)
  3. washThe pad was washed with EtOH (10 ml)
  4. concentrationconcentrated in vacuo
  5. customto afford a dark yellow powder

Sources & evidence

ORD record
ord-818e18d80cbf45c5b7029a7f628a70dd
Source dataset
uspto-grants-2010_03
Patent number
US07683091B2

Reaction notes

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