Dimethylformamide → HCID 68119267, compound

HRID 2398554Notes

Reaction equation

HRID 2398554 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]([S:21]([CH3:24])(=[O:23])=[O:22])=[CH:19][CH:20]=[C:13]3[C:12]2=[O:25])[CH:5]=1)([O-])=O.CN(C)C=O.[H][H]>[Pd].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]([S:21]([CH3:24])(=[O:23])=[O:22])=[CH:19][CH:20]=[C:13]3[C:12]2=[O:25])[CH:5]=1

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 68119789HCID 68119789, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 68119267HCID 68119267, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

The mixture of 2.5 g of N-(4- nitro-o-tolyl)-4-methylsulfonylphthalimide, 0.1 g of palladium on carbon, 80 ml of dimethylformamide and 200 ml of ethyl acetate is hydrogenated at 2.7 atm. and room temperature until the hydrogen uptake ceases. It is filtered, the filtrate extracted with hydrochloric acid, washed with ethyl acetate, basified with sodium carbonate, reextracted with ethyl acetate, the organic solution washed with water, dried filtered and evaporated. The residue is triturated with ethyl acetate-diethyl ether, to yield the N-(4-amino-o-tolyl)-4-methylsulfonylphthalimide melting at 214°-220°.

Workup

  1. filtrationIt is filtered
  2. extractionthe filtrate extracted with hydrochloric acid
  3. washwashed with ethyl acetate
  4. washthe organic solution washed with water
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue is triturated with ethyl acetate-diethyl ether

Sources & evidence

ORD record
ord-2f84d1c45e6241c79253f809c1793e36
Source dataset
uspto-grants-1977_05
Patent number
US04025505

Reaction notes

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