5-(2-Nitrobenzoyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-pyrazole → 5-(2-Aminobenzoyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-pyrazole

HRID 2330Notes

Reaction equation

HRID 2330 reaction equation
[N+:1]([C:4]1[CH:24]=[CH:23][CH:22]=[CH:21][C:5]=1[C:6]([C:8]1[N:12]([CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:20])([CH3:19])[CH3:18])[N:11]=[CH:10][CH:9]=1)=[O:7])([O-])=O>C1COCC1>[NH2:1][C:4]1[CH:24]=[CH:23][CH:22]=[CH:21][C:5]=1[C:6]([C:8]1[N:12]([CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:19])([CH3:20])[CH3:18])[N:11]=[CH:10][CH:9]=1)=[O:7]

Participants

3

Reactant 1

HCID 152820185-(2-Nitrobenzoyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-pyrazole

Product 1

HCID 152820205-(2-Aminobenzoyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-pyrazoleYield 49%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The mixture of pyrazoles of examples 13C and 13D (2.35 g, 6.772 mmol) was taken up in dry THF (100 ml) and degassed. 5% Pd.-on-carbon (1.2 g) was added and the mixture hydrogenated at 30 psi and ambient temperature for 2 h. The mixture was filtered (celite filter aid) and evaporated and then chromatographed (eluant 30% EtOAc in hexanes) to provide the two tide compounds as an equimolar mixture (1.05 g, 49%).

Workup

  1. customdegassed
  2. addition-on-carbon (1.2 g) was added
  3. filtrationThe mixture was filtered
  4. filtration(celite filter aid)
  5. customevaporated
  6. customchromatographed (eluant 30% EtOAc in hexanes)

Sources & evidence

ORD record
ord-640b83ec08f243538919c6f734081f30
Source dataset
uspto-grants-1998_03
Patent number
US05728829

Reaction notes

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