HCID 70621885, compound → HCID 70622246, compound

HRID 267360Notes

Reaction equation

HRID 267360 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]([Cl: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]([Cl:21])[CH:18]=[CH:19][CH:20]=[C:13]3[C:12]2=[O:22])[CH:5]=1

Participants

5

Reactant 2

HCID 70621885HCID 70621885, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 70622246HCID 70622246, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8857Ethyl AcetateSolvent

Procedure

The mixture of 1.65 g of N-(4-nitro-o-tolyl)-3-chlorophthalimide, 200 ml of ethyl acetate and 0.92 g of pre-washed Raney nickel is hydrogenated at 3.1 atm. and room temperature until the hydrogen uptake ceases. It is filtered, evaporated and the residue recrystallized from methanol, to yield the N-(4-amino-o-tolyl)-3-chlorophthalimide melting at 209°-211°.

Workup

  1. filtrationIt is filtered
  2. customevaporated
  3. customthe residue recrystallized from methanol

Sources & evidence

ORD record
ord-d7b7cea381834c00a85f519451e946ae
Source dataset
uspto-grants-1976_03
Patent number
US03941883

Reaction notes

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