HCID 787234, compound → HCID 6611295, compound

HRID 2398566Notes

Reaction equation

HRID 2398566 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]([C:21]([OH:23])=[O:22])=[CH:19][CH:20]=[C:13]3[C:12]2=[O:24])[CH:5]=1)([O-])=O>C(OCC)(=O)C.[Pt]=O>[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]([C:21]([OH:23])=[O:22])=[CH:19][CH:20]=[C:13]3[C:12]2=[O:24])[CH:5]=1

Participants

4

Reactant 1

HCID 787234HCID 787234, compound

Product 1

HCID 6611295HCID 6611295, compound

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 8857Ethyl AcetateSolvent

Procedure

The solution of 4.0 g of N-(4-nitro-o-tolyl)-4-carboxyphthalimide in 200 ml of ethyl acetate is hydrogenated over 1.0 g of platinum oxide at 2.5 atm. and about 40° for 50 minutes. The suspension obtained is evaporated, the residue taken up in 50 ml of dimethylformamide, the mixture filtered, the filtrate evaporated and the residue triturated with 100 ml of ethanol, to yield the N-(4-amino-o-tolyl)-4-carboxyphthalimide melting at 280°. Analogously the N-(4-amino-o-tolyl)-4-carbomethoxyphthalimide is prepared, melting after recrystallization from ethyl acetate-diethyl ether at 161°-162°.

Workup

  1. customThe suspension obtained
  2. customis evaporated
  3. filtrationthe mixture filtered
  4. customthe filtrate evaporated
  5. customthe residue triturated with 100 ml of ethanol

Sources & evidence

ORD record
ord-25dd7bdabf474ea79606872bae5b7288
Source dataset
uspto-grants-1977_05
Patent number
US04025505

Reaction notes

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