HCID 19862778, compound → HCID 19862783, compound

HRID 1165267Notes

Reaction equation

HRID 1165267 reaction equation
[CH2:1]([O:5][C:6](=[O:19])[C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][C:8]=1[N+:16]([O-])=O)[CH:2]([CH3:4])[CH3:3].[H][H]>[Pd].CO>[CH2:1]([O:5][C:6](=[O:19])[C:7]1[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][C:8]=1[NH2:16])[CH:2]([CH3:4])[CH3:3]

Participants

5

Reactant 2

HCID 19862778HCID 19862778, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 19862783HCID 19862783, compoundYield 81.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A 500 ml Parr Shaker was charged with 80.0 g of isobutyl-2,4-dinitrobenzoate, 200 ml methanol, and 3.0 g of a 5% palladium on carbon/50% water catalyst. The mixture was hydrogenated at 50 psi hydrogen pressure while maintaining the temperature below 50° C. Hydrogen uptake cease after 4 hrs. The mixture was cooled, filtered and the methanol removed under reduced pressure. The remaining solid was washed with toluene, filtered and dried to give 50.7 g of isobutyl-2,4-diaminobenzoate, a light tan solid, mp 89° C.

Workup

  1. temperaturewhile maintaining the temperature below 50° C
  2. temperatureThe mixture was cooled
  3. filtrationfiltered
  4. customthe methanol removed under reduced pressure
  5. washThe remaining solid was washed with toluene
  6. filtrationfiltered
  7. customdried

Sources & evidence

ORD record
ord-1bb59fbc0d4b43a9955aa9a81f3e9121
Source dataset
uspto-grants-1990_03
Patent number
US04908394

Reaction notes

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