1-(4-methylbenzyl)-3-nitro-1H-pyrazole → HCID 571039, compound

HRID 546030

Reaction equation

HRID 546030 reaction equation
[CH3:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][N:7]2[CH:11]=[CH:10][C:9]([N+:12]([O-])=O)=[N:8]2)=[CH:4][CH:3]=1>O1CCCC1.NN.[Ni]>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[CH:11]=[CH:10][C:9]([NH2:12])=[N:8]2)=[CH:15][CH:16]=1

Participants

5

Reactant 1

HCID 70101741-(4-methylbenzyl)-3-nitro-1H-pyrazole

Product 1

HCID 571039HCID 571039, compound

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent2×HCID 9321HydrazineSolvent

Procedure

To a solution containing 1-(4-methyl-benzyl)-3-nitro-1H-pyrazole (92 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-(4-methyl-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-f11207cfe36b4a66a84f0f32ba581c7f
Source dataset
uspto-grants-2011_05
Patent number
US07935699B2

Linked notes

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