HCID 4017380, compound → HCID 22501979, compound

HRID 1814709Notes

Reaction equation

HRID 1814709 reaction equation
[CH:1]([N:4]1[C:8](=[O:9])[C:7]2=[CH:10][C:11]([N+:14]([O-])=O)=[CH:12][CH:13]=[C:6]2[C:5]1=[O:17])([CH3:3])[CH3:2]>C1COCC1.CN(C=O)C.[Pd]>[CH:1]([N:4]1[C:8](=[O:9])[C:7]2=[CH:10][C:11]([NH2:14])=[CH:12][CH:13]=[C:6]2[C:5]1=[O:17])([CH3:3])[CH3:2]

Participants

5

Reactant 1

HCID 4017380HCID 4017380, compound

Product 1

HCID 22501979HCID 22501979, compoundYield 99.1%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

N-Isopropyl-4-nitrophthalimide (10.0 g, 43.0 mmol) was dissolved in a mixture of THF (200 mL) and DMF (100 mL). 10% Palladium catalyst on carbon (1,0 g, 50% wet weight) was added and the mixture was hydrogenated in a low-pressure apparatus (1 atm.) overnight. The catalyst was then removed by filtering the mixture through a short pad of celite. The filtrate was evaporated to dryness to afford a quantitative yield (8.70 g) of pure N-isopropyl-4-aminophthalimide.

Workup

  1. customwas hydrogenated in a low-pressure apparatus (1 atm.) overnight
  2. customThe catalyst was then removed
  3. filtrationby filtering the mixture through a short pad of celite
  4. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-f403f52d126e4acf8bc7d514a0ead29d
Source dataset
uspto-grants-2005_04
Patent number
US06875760B2

Reaction notes

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