HCID 68119851, compound → HCID 68119881, compound

HRID 267358Notes

Reaction equation

HRID 267358 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=[C:17]([CH3:21])[CH:18]=[CH:19][CH:20]=[C:13]3[C:12]2=[O:22])[CH:5]=1)([O-])=O.[H][H]>[Ni].C(OCC)(=O)C>[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=[C:17]([CH3:21])[CH:18]=[CH:19][CH:20]=[C:13]3[C:12]2=[O:22])[CH:5]=1

Participants

5

Reactant 2

HCID 68119851HCID 68119851, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 68119881HCID 68119881, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8857Ethyl AcetateSolvent

Procedure

The mixture of 3.94 g of N-(4-nitro-o-tolyl)-3-methylphthalimide, 200 ml of ethyl acetate and 2.2 g of Raney nickel (pre-washed with water and ethyl acetate) is hydrogenated at 3.1 atm. and room temperature until the hydrogen uptake ceases. It is filtered, evaporated, the residue triturated with chloroform, filtered again, the filtrate evaporated and the residue recrystallized from methanol, to yield the N-(4-amino-o-tolyl)-3-methylphthalimide of the formula ##SPC5##

Workup

  1. filtrationIt is filtered
  2. customevaporated
  3. customthe residue triturated with chloroform
  4. filtrationfiltered again
  5. customthe filtrate evaporated
  6. customthe residue recrystallized from methanol

Sources & evidence

ORD record
ord-b9211536ee9b427ab2f0f96cbf03fe8f
Source dataset
uspto-grants-1976_03
Patent number
US03941883

Reaction notes

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