1-(4-Methoxybenzyl)-4-nitro-1H-pyrazole → 1-((4-methoxyphenyl)methyl)-1H-pyrazol-4-amine

HRID 1406393Notes

Reaction equation

HRID 1406393 reaction equation
[CH3:1][O:2][C:3]1[CH:17]=[CH:16][C:6]([CH2:7][N:8]2[CH:12]=[C:11]([N+:13]([O-])=O)[CH:10]=[N:9]2)=[CH:5][CH:4]=1>C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][N:8]2[CH:12]=[C:11]([NH2:13])[CH:10]=[N:9]2)=[CH:16][CH:17]=1

Participants

3

Reactant 1

HCID 666114661-(4-Methoxybenzyl)-4-nitro-1H-pyrazole

Product 1

HCID 283739871-((4-methoxyphenyl)methyl)-1H-pyrazol-4-amine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-(4-Methoxy-benzyl)-4-nitro-1H-pyrazole (240 mg, 1.03 mmol) was stirred in ethanol (10 mL) and the flask was evacuated and then flushed with nitrogen. Platinum, sulfided, 5 wt. % on carbon, reduced, dry (10 mg, catalytic amount) was added and after two vacuum/H2 cycles to replace the nitrogen inside with hydrogen, the mixture was shaken for 18 hours under ordinary hydrogen pressure (1 atm). The reaction mixture was filtered and the filtrate was concentrated in vacuo to yield a red oil, which was used without further purification, 168 mg, 81%.

Workup

  1. customthe flask was evacuated
  2. customflushed with nitrogen
  3. customdry (10 mg, catalytic amount)
  4. additionwas added
  5. filtrationThe reaction mixture was filtered
  6. concentrationthe filtrate was concentrated in vacuo
  7. customto yield a red oil, which
  8. customwas used without further purification, 168 mg, 81%

Sources & evidence

ORD record
ord-61c95d3006e44936a0a715da48a27938
Source dataset
uspto-grants-2014_12
Patent number
US08916591B2

Reaction notes

Loading…