1,3,5-Trimethyl-4-nitro-1H-pyrazole → 1,3,5-trimethyl-1H-pyrazol-4-amine

HRID 1938679

Reaction equation

HRID 1938679 reaction equation
[N+:1]([C:4]1[C:5]([CH3:11])=[N:6][N:7]([CH3:10])[C:8]=1[CH3:9])([O-])=O>[Ni].N>[NH2:1][C:4]1[C:5]([CH3:11])=[N:6][N:7]([CH3:10])[C:8]=1[CH3:9]

Participants

4

Reactant 1

HCID 1210191,3,5-Trimethyl-4-nitro-1H-pyrazole

Product 1

HCID 1616031,3,5-trimethyl-1H-pyrazol-4-amine

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 222AmmoniaSolvent

Procedure

The compounds from (b) above (2.3 g; 0.014 moles) was catalytically hydrogenated using Raney nickel (1 g) in methanolic ammonia (100 mL) under a hydrogen atmosphere at 50 psi. The catalyst was filtered and the solution concentrated in vacuo, leaving a residue that was triturated several times with ethyl ether. The decanted solvent was concentrated to dryness, leaving a pale red solid. Yield: 1.3 g (70%).

Workup

  1. filtrationThe catalyst was filtered
  2. concentrationthe solution concentrated in vacuo
  3. customleaving a residue that
  4. customwas triturated several times with ethyl ether
  5. concentrationThe decanted solvent was concentrated to dryness
  6. customleaving a pale red solid

Sources & evidence

ORD record
ord-7499a540f9324c048fff25eb22982f83
Source dataset
uspto-grants-1997_12
Patent number
US05693657

Linked notes

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