HCID 86733104, compound → HCID 54892955, compound

HRID 2398551Notes

Reaction equation

HRID 2398551 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[C:6]([N:11]2[C:20](=[O:21])[C:19]3[C:14](=[N:15][CH:16]=[CH:17][CH:18]=3)[C:12]2=[O:13])[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:20](=[O:21])[C:19]3[C:14](=[N:15][CH:16]=[CH:17][CH:18]=3)[C:12]2=[O:13])[CH:5]=1

Participants

5

Reactant 2

HCID 86733104HCID 86733104, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 54892955HCID 54892955, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8857Ethyl AcetateSolvent

Procedure

The mixture of 2.83 g of N-(4-nitro-o-tolyl)-pyridine-2,3-dicarboximide, 200 ml of ethyl acetate and 1.6 g of prewashed Raney nickel is hydrogenated at 3.1 atm. and room temperature until the hydrogen uptake ceases. It is filtered, evaporated, the residue taken up in chloroform, the solution treated with charcoal, filtered, evaporated and the residue recrystallized from methanol, to yield the N-(4-amino-o-tolyl)-pyridine-2,3-dicarboximide of the formula ##STR6## melting at 180°-182°.

Workup

  1. filtrationIt is filtered
  2. customevaporated
  3. additionthe solution treated with charcoal
  4. filtrationfiltered
  5. customevaporated
  6. customthe residue recrystallized from methanol

Sources & evidence

ORD record
ord-b30ac953028940fbbb32cd0c8be1750f
Source dataset
uspto-grants-1977_05
Patent number
US04025505

Reaction notes

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