Water → 1,3-Dimethyl-1H-indazol-5-amine

HRID 1022183Notes

Reaction equation

HRID 1022183 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)[C:4]([CH3:14])=[N:3]1.NN.O>C(O)C.[Pd]>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([NH2:11])=[CH:8][CH:9]=2)[C:4]([CH3:14])=[N:3]1

Participants

6

Reactant 3

HCID 962WaterHCID 9321HydrazineHCID 2909341,3-Dimethyl-5-nitro-1h-indazole

Product 1

HCID 588560951,3-Dimethyl-1H-indazol-5-amineYield 84.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 307a (crude, 2.5 mmol) in ethanol (95%, 30 mL) was added NH2NH2.water (1.25 g, 25.0 mmol), Pd/C (100 mg) under nitrogen protection. The mixture was stirred at 50° C. for 1.5 h. It was then cooled to room temperature and filtered through a pad of CELITE®. The filtrate was concentrated under reduced pressure and the residue was recrystallized from anhydrous ethanol (5 mL) to afford 307b as white solid (340 mg, 84% over two steps). MS-ESI: [M+H]+ 162.3

Workup

  1. temperatureIt was then cooled to room temperature
  2. filtrationfiltered through a pad of CELITE®
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customthe residue was recrystallized from anhydrous ethanol (5 mL)

Sources & evidence

ORD record
ord-2f488ec7181b49cd99afba6c5746ec6c
Source dataset
uspto-grants-2014_05
Patent number
US08716274B2

Reaction notes

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