HCID 53729442, compound → HCID 54259855, compound

HRID 1165265Notes

Reaction equation

HRID 1165265 reaction equation
[CH3:1][O:2][CH2:3][CH:4]([O:6][C:7](=[O:20])[C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[CH:10][C:9]=1[N+:17]([O-])=O)[CH3:5].[H][H]>[Pd].CO>[CH3:1][O:2][CH2:3][CH:4]([O:6][C:7](=[O:20])[C:8]1[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][C:9]=1[NH2:17])[CH3:5]

Participants

5

Reactant 2

HCID 53729442HCID 53729442, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 54259855HCID 54259855, compoundYield 93.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A 500 ml Parr Shaker was charged with 75.6 g of (1-methoxy-2-propyl)-2,4-dinitrobenzoate, 200 ml methanol, and 1.5 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 ceased after 4 hrs. The mixture was cooled, filtered, and the methanol removed under reduced pressure to give 56 g of (1-methoxy-2-propyl)-2,4-diaminobenzoate, a brown viscous liquid.

Workup

  1. temperaturewhile maintaining the temperature below 50° C
  2. temperatureThe mixture was cooled
  3. filtrationfiltered
  4. customthe methanol removed under reduced pressure

Sources & evidence

ORD record
ord-bbd5d370eb1f444e8c072496311a397c
Source dataset
uspto-grants-1990_03
Patent number
US04908394

Reaction notes

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