HCID 4572529, compound → HCID 63303484, compound

HRID 2398562Notes

Reaction equation

HRID 2398562 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[CH:18]=[CH:17][N:16]=[CH:15][C:14]=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[CH:18]=[CH:17][N:16]=[CH:15][C:14]=3[C:12]2=[O:13])[CH:5]=1

Participants

5

Reactant 2

HCID 4572529HCID 4572529, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 63303484HCID 63303484, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8857Ethyl AcetateSolvent

Procedure

The mixture of 2.5 g of N-(4-nitro-o-tolyl)-pyridine-3,4- dicarboximide, 1.2 g of Raney nickel and 575 ml of ethyl acetate is hydrogenated at 3.4 atm. and room temperature until the hydrogen uptake ceases. It is filtered, evaporated and the residue thoroughly leached with hot benzene. The filtrate is evaporated, the residue chromatographed on silica gel and eluted with ethyl acetate, to yield the N-(4-amino-o-tolyl)-pyridine-3,4-dicarboximide as an oil, the mass spectrum of which shows the expected molecular ion of 253.

Workup

  1. filtrationIt is filtered
  2. customevaporated
  3. customThe filtrate is evaporated
  4. customthe residue chromatographed on silica gel
  5. washeluted with ethyl acetate

Sources & evidence

ORD record
ord-26670ba23e054f64a61bcfbd7885ab47
Source dataset
uspto-grants-1977_05
Patent number
US04025505

Reaction notes

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