N,N,2-trimethyl-1-(3-nitro-1H-pyrazol-1-yl)propan-2-amine → 1-[2-(Dimethylamino)-2-methylpropyl]-1H-pyrazol-3-amine

HRID 1844539Notes

Reaction equation

HRID 1844539 reaction equation
[CH3:1][N:2]([CH3:15])[C:3]([CH3:14])([CH3:13])[CH2:4][N:5]1[CH:9]=[CH:8][C:7]([N+:10]([O-])=O)=[N:6]1>[C].[Pd].C(O)C.C(OCC)(=O)C>[CH3:1][N:2]([CH3:15])[C:3]([CH3:13])([CH3:14])[CH2:4][N:5]1[CH:9]=[CH:8][C:7]([NH2:10])=[N:6]1

Participants

4

Reactant 1

HCID 66880823N,N,2-trimethyl-1-(3-nitro-1H-pyrazol-1-yl)propan-2-amine

Product 1

HCID 583285031-[2-(Dimethylamino)-2-methylpropyl]-1H-pyrazol-3-amineYield 94%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 21584252Ethanol ethylacetateSolvent

Procedure

N,N,2-trimethyl-1-(3-nitro-1H-pyrazol-1-yl)propan-2-amine (70.6 mg) was dissolved in a mixed solution (ethanol-ethyl acetate, 4:1, 5 mL). Then, 10% palladium-carbon (7 mg) was added to the prepared solution, and the solution was subjected to catalytic reduction at 101 kPa for about 2 hours. The reaction mixture was filtrated through Celite, and the filtrate was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (silica gel NH, ethyl acetate:hexane=1:1) to give the title compound as a yellow oil (56.8 mg, yield: 94%).

Workup

  1. filtrationThe reaction mixture was filtrated through Celite
  2. customthe filtrate was evaporated under reduced pressure
  3. customThe obtained residue was purified by silica gel column chromatography (silica gel NH, ethyl acetate:hexane=1:1)

Sources & evidence

ORD record
ord-7017e47eadb446ed878822deea378193
Source dataset
uspto-grants-2015_02
Patent number
US08946440B2

Reaction notes

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