4-Nitro-1-p-tolyl-1H-pyrazole → 4-Amino-1-p-tolyl-1H-pyrazole

HRID 75578Notes

Reaction equation

HRID 75578 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][N:7]([C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=2)[CH:8]=1)([O-])=O>C(O)C.[Pd]>[NH2:1][C:4]1[CH:5]=[N:6][N:7]([C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=2)[CH:8]=1

Participants

4

Reactant 1

HCID 114130304-Nitro-1-p-tolyl-1H-pyrazole

Product 1

HCID 218128244-Amino-1-p-tolyl-1H-pyrazoleYield 86%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Intermediate 6a (212 mg, 1.04 mmol) was dissolved in ethanol (20 mL) then hydrogenated over 10% palladium on carbon for 4 h under hydrogen atmosphere. The mixture was then filtered through Celite, washing with ethanol, and evaporated to dryness. The residue was purified by FCC, eluting with 0-10% MeOH in DCM, to give the title compound as a pale brown solid (154 mg, 86%). LCMS (Method 3): Rt 1.92 min, m/z 174.1 [MH−].

Workup

  1. filtrationThe mixture was then filtered through Celite
  2. washwashing with ethanol
  3. customevaporated to dryness
  4. customThe residue was purified by FCC
  5. washeluting with 0-10% MeOH in DCM

Sources & evidence

ORD record
ord-0a7a392b929240649a560159c1c399f7
Source dataset
uspto-grants-2014_09
Patent number
US08835431B2

Reaction notes

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