HCID 13589233, compound → HCID 178432041, compound

HRID 568808Notes

Reaction equation

HRID 568808 reaction equation
[C:1]([NH:4][C:5]1[CH:13]=[C:12]2[C:8]([C:9]([CH3:16])([CH3:15])[C:10](=[O:14])[NH:11]2)=[CH:7][C:6]=1[N+:17]([O-])=O)(=O)[CH3:2].[H][H]>[Pt](=O)=O.C(O)(=O)C>[CH3:2][C:1]1[NH:4][C:5]2[CH:13]=[C:12]3[NH:11][C:10](=[O:14])[C:9]([CH3:16])([CH3:15])[C:8]3=[CH:7][C:6]=2[N:17]=1

Participants

5

Reactant 2

HCID 13589233HCID 13589233, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 178432041HCID 178432041, compound

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolvent

Procedure

Analogously to Example 5, 5.00 g. (0.019 mole) 6-acetamido-5-nitro-3,3-dimethylindolin-2-one are suspended in 900 ml. glacial acetic acid and hydrogenated in the presence of 0.5 g. platinum dioxide at normal pressure and ambient temperature. After 1.4 liters of hydrogen have been taken up, the reaction mixture is filtered and the filtrate is evaporated to dryness in a vacuum. The residue is taken up in water and neutralised with a 2N aqueous ammonia solution. The precipitate obtained is filtered off with suction and recrystallised from ethyl acetate. There are obtained 2.75 g. (67% of theory) of the title compound; m.p. >300° C.

Workup

  1. customat normal pressure and ambient temperature
  2. filtrationthe reaction mixture is filtered
  3. customthe filtrate is evaporated to dryness in a vacuum
  4. customThe precipitate obtained
  5. filtrationis filtered off with suction
  6. customrecrystallised from ethyl acetate
  7. customThere are obtained 2.75 g

Sources & evidence

ORD record
ord-9f30dd88eab54569b73b5c984da7c763
Source dataset
uspto-grants-1988_03
Patent number
US04730003

Reaction notes

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