HCID 54283452, compound → HCID 53663414, compound

HRID 2398556Notes

Reaction equation

HRID 2398556 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:14](=[O:15])[C:13]3=[CH:16][C:17]([Cl:20])=[CH:18][CH:19]=[C:12]3[C:11]2=[O:21])=[C:6]([CH2:22][S:23][CH3:24])[CH:5]=1)([O-])=O.[H][H]>[Ni].C(OCC)(=O)C>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:14](=[O:15])[C:13]3=[CH:16][C:17]([Cl:20])=[CH:18][CH:19]=[C:12]3[C:11]2=[O:21])=[C:6]([CH2:22][S:23][CH3:24])[CH:5]=1

Participants

5

Reactant 2

HCID 54283452HCID 54283452, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 53663414HCID 53663414, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8857Ethyl AcetateSolvent

Procedure

The mixture of 3.0 g of N-(4-nitro-2-methylmercaptomethylphenyl)-4-chlorophthalimide, 1.5 g of Raney nickel and 250 ml of ethyl acetate is hydrogenated at room temperature and atmospheric pressure until the hydrogen uptake ceases. It is filtered, the filtrate evaporated and the residue recrystallized from benzene, to yield the N-(4-amino-2-methylmercaptomethylphenyl)-4-chlorophthalimide melting at 134°-137°. Analogously the N-(4-amino-2-methylsulfonylmethylphenyl)-4-chlorophthalimide is prepared, m.p. 253°-257° (acetonitrile); as well as the N-(4-amino-2-hydroxymethylphenyl)-4-chlorophthalimide, m.p. 228°-230° (ethyl acetatediethyl ether).

Workup

  1. customis hydrogenated at room temperature
  2. filtrationIt is filtered
  3. customthe filtrate evaporated
  4. customthe residue recrystallized from benzene

Sources & evidence

ORD record
ord-65f30ebbd82d43d5a98f80c6b8bcb1b6
Source dataset
uspto-grants-1977_05
Patent number
US04025505

Reaction notes

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