HCID 7172345, compound → HCID 7019302, compound

HRID 546036Notes

Reaction equation

HRID 546036 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][C:16]=1[Cl:17])[CH2:5][N:6]1[CH:10]=[CH:9][C:8]([N+:11]([O-])=O)=[N:7]1>O1CCCC1.NN.[Ni]>[Cl:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][C:16]=1[Cl:17])[CH2:5][N:6]1[CH:10]=[CH:9][C:8]([NH2:11])=[N:7]1

Participants

5

Reactant 1

HCID 7172345HCID 7172345, compound

Product 1

HCID 7019302HCID 7019302, compound

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent2×HCID 9321HydrazineSolvent

Procedure

To a solution containing 1-(3,4-dichloro-benzyl)-3-nitro-1H-pyrazole (115 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 1-(3,4-dichloro-benzyl)-1H-pyrazol-3-ylamine as a yellow oil which was used in the following 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-8c89a3e5c73441a28cf50907af61a74e
Source dataset
uspto-grants-2011_05
Patent number
US07935699B2

Reaction notes

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