Ethanol → HCID 43345922, compound

HRID 267359Notes

Reaction equation

HRID 267359 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-584f793e949f4240bc48877347c8340c
Source dataset
uspto-grants-1976_03
Patent number
US03941883

Reaction notes

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