HCID 70622593, compound → HCID 70621330, compound

HRID 267361Notes

Reaction equation

HRID 267361 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]([Cl:21])=[CH:19][CH:20]=[C:13]3[C:12]2=[O:22])[CH:5]=1)([O-])=O>[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=[CH:17][C:18]([Cl:21])=[CH:19][CH:20]=[C:13]3[C:12]2=[O:22])[CH:5]=1

Participants

4

Reactant 1

HCID 70622593HCID 70622593, compound

Product 1

HCID 70621330HCID 70621330, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8857Ethyl AcetateSolvent

Procedure

The mixture of 12.4 g of N-(4-nitro-o-tolyl)-4-chlorophthalimide, 1.0 lt. ethyl acetate and 10 ml of an ethanolic suspension containing 6.9 g of Raney nickel is hydrogenated at 2.8 atm. and room temperature for 12 hours. It is filtered, concentrated to about half of its original volume and the precipitate formed collected, to yield the N-(4-amino-o-tolyl)-4-chlorophthalimide melting at 201°-203°. Its 4-bromo-analog melts at 208°-211°.

Workup

  1. filtrationIt is filtered
  2. concentrationconcentrated to about half of its original volume
  3. customthe precipitate formed
  4. customcollected

Sources & evidence

ORD record
ord-774963a67656402fbbe454c01c4d479f
Source dataset
uspto-grants-1976_03
Patent number
US03941883

Reaction notes

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