HCID 21272635, compound → HCID 178429206, compound

HRID 1193574Notes

Reaction equation

HRID 1193574 reaction equation
[C:1]([NH:9][C:10]1[CH:18]=[C:17]2[C:13]([C:14]([CH3:21])([CH3:20])[C:15](=[O:19])[NH:16]2)=[CH:12][C:11]=1[N+:22]([O-])=O)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H][H]>[Pd].C(O)(=O)C>[CH3:20][C:14]1([CH3:21])[C:13]2[C:17](=[CH:18][C:10]3[NH:9][C:1]([C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)=[N:22][C:11]=3[CH:12]=2)[NH:16][C:15]1=[O:19]

Participants

5

Reactant 2

HCID 21272635HCID 21272635, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 178429206HCID 178429206, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

1.0 g. palladium/charcoal (10%) were introduced into 10.0 g. (30.7 mmol) 6-benzoylamino-5-nitro-3,3-dimethylindolin-2-one in 250 ml. glacial acetic acid. This mixture was hydrogenated in a shaking bomb at ambient temperature and normal pressure. After the take up of hydrogen had ceased, the solution was separated from the catalyst, slowly evaporated at 60° C. and the residue taken up in water and neutralised with 2N aqueous ammonia solution. The precipitate was filtered off with suction and recrystallised from methylene chloride. There were obtained 6.9 g. (81% of theory) of the title compound; m.p. 195°-220° C.

Workup

  1. customwas hydrogenated in a shaking bomb at ambient temperature
  2. customthe solution was separated from the catalyst
  3. customslowly evaporated at 60° C.
  4. filtrationThe precipitate was filtered off with suction
  5. customrecrystallised from methylene chloride
  6. customThere were obtained 6.9 g

Sources & evidence

ORD record
ord-5a42d80cd95e4e83acd1d459b650a18e
Source dataset
uspto-grants-1989_03
Patent number
US04810801

Reaction notes

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