HCID 70622593, compound → HCID 70621330, compound

HRID 2398563Notes

Reaction equation

HRID 2398563 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 solution of 416 g of N-(4-nitro-o-tolyl)-4-chlorophthalimide in 28 lt. of hot ethyl acetate is cooled slightly and transferred under nitrogen to 250 ml (or 460 g) of a suspension of Raney nickel, which has been washed 4 times with anhydrous ethanol and 1 time with ethyl acetate, and 12 lt of ethyl acetate are used for the rinse. The mixture is hydrogenated at 3.4 atm. and 30° for approximately 8 hours, and continued for 2 hours after the hydrogen uptake has ceased. It is filtered, the residue rinsed with 15 lt. of ethyl acetate and the filtrate concentrated to about 14 lt. It is cooled, filtered, and the filtrate reduced to approximately 11/2 lt to yield 2 crops of N-(4-amino-o-tolyl)-4-chlorophthalimide melting at 205°-207°; it is identical (but somewhat purer) than that obtained according to Example 4.

Workup

  1. washhas been washed 4 times with anhydrous ethanol and 1 time with ethyl acetate, and 12 lt of ethyl acetate
  2. waitcontinued for 2 hours
  3. filtrationIt is filtered
  4. washthe residue rinsed with 15 lt
  5. concentrationof ethyl acetate and the filtrate concentrated to about 14 lt
  6. temperatureIt is cooled
  7. filtrationfiltered

Sources & evidence

ORD record
ord-38ac25ef4701430bb200f7bb3c8a1a1c
Source dataset
uspto-grants-1977_05
Patent number
US04025505

Reaction notes

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