Hydrazine hydrate (1:1) → 1-Methylindolin-5-amine

HRID 2104296Notes

Reaction equation

HRID 2104296 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([N+:11]([O-])=O)=[CH:8][CH:9]=2)[CH2:4][CH2:3]1.O.NN>[Ni].C(O)C>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([NH2:11])=[CH:8][CH:9]=2)[CH2:4][CH2:3]1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 1677381H-Indole, 2,3-dihydro-1-methyl-5-nitro-

Product 1

HCID 226371221-Methylindolin-5-amine

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

Approximately 400 mg of Raney nickel is added to a mixture of 2.84 g (15.9 mmol) of 1-methyl-5-nitroindoline and 4 ml (80 mmol) of hydrazine hydrate in-60 ml of absolute ethanol. The reaction mixture is heated to reflux for 5 hours. After returning to 23° C., a little silica is added to the flask and the solvent is evaporated off under vacuum. The evaporation residue is placed directly at the top of a chromatography column. The expected product is eluted using a Heptane/AcOEt mixture (3/7). A violet powder is obtained (65%) which is used directly in the following stage.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureto reflux for 5 hours
  3. customAfter returning to 23° C.
  4. additiona little silica is added to the flask
  5. customthe solvent is evaporated off under vacuum
  6. washThe expected product is eluted
  7. customA violet powder is obtained (65%) which

Sources & evidence

ORD record
ord-0356d989b0bd4cfd92f3f322541e7ca3
Source dataset
uspto-grants-2009_08
Patent number
US07576241B2

Reaction notes

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