HCID 20149423, compound → HCID 178429218, compound

HRID 568807Notes

Reaction equation

HRID 568807 reaction equation
[F:1][C:2]([F:22])([F:21])[C:3]([NH:5][C:6]1[CH:14]=[C:13]2[C:9]([C:10]([CH3:17])([CH3:16])[C:11](=[O:15])[NH:12]2)=[CH:8][C:7]=1[N+:18]([O-])=O)=O>[Pd].C(O)C>[CH3:16][C:10]1([CH3:17])[C:9]2[C:13](=[CH:14][C:6]3[NH:5][C:3]([C:2]([F:22])([F:21])[F:1])=[N:18][C:7]=3[CH:8]=2)[NH:12][C:11]1=[O:15]

Participants

4

Reactant 1

HCID 20149423HCID 20149423, compound

Product 1

HCID 178429218HCID 178429218, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Analogously to Example 5, 4.50 g. (0.014 mole) 6-trifluoroacetamido-5-nitro-3,3-dimethylindolin-2-one in 500 ml. ethanol are hydrogenated in the presence of 0.5 g. 10% palladium on charcoal at normal pressure and at ambient temperature. After filtration, the filtrate is evaporated to dryness in a vacuum and the residue is dissolved in dichloromethane/ethyl acetate and treated with active charcoal. After filtration, the filtrate is evaporated to dryness in a vacuum and the residue is recrystallised from ethyl acetate, there being obtained 3.8 g. (95% of theory) of the title compound in the form of the monohydrate; m.p. 175°-177° C.

Workup

  1. customat ambient temperature
  2. filtrationAfter filtration
  3. customthe filtrate is evaporated to dryness in a vacuum
  4. dissolutionthe residue is dissolved in dichloromethane/ethyl acetate
  5. additiontreated with active charcoal
  6. filtrationAfter filtration
  7. customthe filtrate is evaporated to dryness in a vacuum
  8. customthe residue is recrystallised from ethyl acetate, there
  9. custombeing obtained 3.8 g

Sources & evidence

ORD record
ord-8fdfc2bc04bf4a288be0cdf7bc11c98e
Source dataset
uspto-grants-1988_03
Patent number
US04730003

Reaction notes

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