Ethanol → HCID 43345922, compound

HRID 2398544Notes

Reaction equation

HRID 2398544 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[C:6]([N:11]2[C:15](=[O:16])[C:14]3=[CH:17][C:18]([CH3:21])=[CH:19][CH:20]=[C:13]3[C:12]2=[O:22])[CH:5]=1)([O-])=O.C(O)C.[H][H]>[Pd].CN(C)C=O>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[C:6]([N:11]2[C:15](=[O:16])[C:14]3=[CH:17][C:18]([CH3:21])=[CH:19][CH:20]=[C:13]3[C:12]2=[O:22])[CH:5]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 68119839HCID 68119839, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 43345922HCID 43345922, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

The mixture of 4.28 g of N-(4-nitro-o-tolyl)-4-methylphthalimide, 200 ml of 95% aqueous ethanol and 0.21 g of 5% palladium on charcoal is hydrogenated at 3.1 atm and 45° until the hydrogen uptake ceases. The resulting suspension is diluted with the minimum amount of dimethylformamide to solubilize the organic material, filtered and evaporated. The residue is taken up in chloroform, the mixture filtered, evaporated and the residue recrystallized from methanol, to yield the N-(4-amino-o-tolyl)-4-methylphthalimide melting at 144°-147°.

Workup

  1. filtrationfiltered
  2. customevaporated
  3. filtrationthe mixture filtered
  4. customevaporated
  5. customthe residue recrystallized from methanol

Sources & evidence

ORD record
ord-ad282d1436bd4c7795340c0026625fbb
Source dataset
uspto-grants-1977_05
Patent number
US04025505

Reaction notes

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