HCID 86713804, compound → HCID 86713803, compound

HRID 521856Notes

Reaction equation

HRID 521856 reaction equation
[CH3:1][N:2]1[C:6]([CH:7](C(OC)=O)[C:8]([O:10][C:11](C)(C)C)=[O:9])=[C:5]([N+:19]([O-:21])=[O:20])[CH:4]=[N:3]1>C(O)=O>[CH3:1][N:2]1[C:6]([CH2:7][C:8]([O:10][CH3:11])=[O:9])=[C:5]([N+:19]([O-:21])=[O:20])[CH:4]=[N:3]1

Participants

3

Reactant 1

HCID 86713804HCID 86713804, compound

Product 1

HCID 86713803HCID 86713803, compoundYield 90.2%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 1-tert-butyl 3-methyl 2-(1-methyl-4-nitro-1H-pyrazol-5-yl)malonate (6.92 g, 23.1 mmol) and formic acid (100 mL) was heated at 50° C. for 5 hours before being cooled to room temperature. Formic acid was removed under reduced pressure; the residue was diluted with brine and extracted with DCM 3×. The combined organics were dried (MgSO4) and the solvent removed under reduced pressure. The residue was purified via silica gel chromatography (0-60% EtOAc/heptane) to afford methyl 2-(2-methyl-4-nitro-pyrazol-3-yl)acetate (4.15 g, 90%).

Workup

  1. temperaturebefore being cooled to room temperature
  2. customFormic acid was removed under reduced pressure
  3. additionthe residue was diluted with brine
  4. extractionextracted with DCM 3×
  5. dry with materialThe combined organics were dried (MgSO4)
  6. customthe solvent removed under reduced pressure
  7. customThe residue was purified via silica gel chromatography (0-60% EtOAc/heptane)

Sources & evidence

ORD record
ord-f02f37651fb84bb1a687dfad4287420f
Source dataset
uspto-grants-2016_05
Patent number
US09328106B2

Reaction notes

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