3-(3-nitro-1H-pyrazol-1-yl)propan-1-ol → 3-(3-amino-1H-pyrazol-1-yl)propan-1-ol

HRID 546018Notes

Reaction equation

HRID 546018 reaction equation
[N+:1]([C:4]1[CH:8]=[CH:7][N:6]([CH2:9][CH2:10][CH2:11][OH:12])[N:5]=1)([O-])=O>O1CCCC1.NN.[Ni]>[NH2:1][C:4]1[CH:8]=[CH:7][N:6]([CH2:9][CH2:10][CH2:11][OH:12])[N:5]=1

Participants

5

Reactant 1

HCID 196218383-(3-nitro-1H-pyrazol-1-yl)propan-1-ol

Product 1

HCID 509897073-(3-amino-1H-pyrazol-1-yl)propan-1-ol

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent2×HCID 9321HydrazineSolvent

Procedure

To a solution containing 3-(3-nitro-pyrazol-1-yl)-propan-1-ol (72 mg, 0.42 mmol) in tetrahydrofuran (2 mL), anhydrous hydrazine (100 μL) was added to the clear solution. Raney nickel (˜100 mg washed 3 times with 5 mL of anhydrous tetrahydrofuran) was then added in tetrahydrofuran (300 μL). Gas evolved from the mixture and the reaction was allowed to proceed for 5 min, after which time the raney nickel was removed by filtration through a celite plug. The solvent was removed in vacuo to afford 3-(3-amino-pyrazol-1-yl)-propan-1-ol as a yellow oil, which was then immediately used in the next step with no further purification.

Workup

  1. additionwas added to the clear solution
  2. customafter which time the raney nickel was removed by filtration through a celite plug
  3. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-1afc62dd100c452589fec169a08eb4d5
Source dataset
uspto-grants-2011_05
Patent number
US07935699B2

Reaction notes

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