HCID 58405813, compound → HCID 57562604, compound

HRID 475077Notes

Reaction equation

HRID 475077 reaction equation
[N+:1]([C:4]1[CH:8]=[CH:7][N:6]([CH2:9][O:10][CH2:11][CH2:12][Si:13]([CH3:16])([CH3:15])[CH3:14])[N:5]=1)([O-])=O>[Pd].CO>[CH3:14][Si:13]([CH3:16])([CH3:15])[CH2:12][CH2:11][O:10][CH2:9][N:6]1[CH:7]=[CH:8][C:4]([NH2:1])=[N:5]1

Participants

4

Reactant 1

HCID 58405813HCID 58405813, compound

Product 1

HCID 57562604HCID 57562604, compoundYield 100.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
30 °C

Procedure

Into a 2 L round-bottom flask purged and maintained with an inert atmosphere of nitrogen was placed 3-nitro-1-[[2-(trimethylsilyl)ethoxy]methyl]-1H-pyrazole (125.0 g, 513.69 mmol, 1.00 equiv.), MeOH (1 L), and Pd/C (13.0 g). The suspension was the placed under an atmosphere of hydrogen. The resulting solution was stirred at 30° C. for 4 h. The solids were then filtered and the filtrate was concentrated under vacuum to afford of 1-[[2-(trimethylsilyl)ethoxy]methyl]-1H-pyrazol-3-amine (110 g 80% yield) as a light yellow solid.

Workup

  1. customInto a 2 L round-bottom flask purged
  2. temperaturemaintained with an inert atmosphere of nitrogen
  3. filtrationThe solids were then filtered
  4. concentrationthe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-d46ff0a58cb44048867b924064093e46
Source dataset
uspto-grants-2014_01
Patent number
US08637537B2

Reaction notes

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