HCID 20149318, compound → HCID 178494634, compound

HRID 568809Notes

Reaction equation

HRID 568809 reaction equation
[CH3:1][O:2][CH2:3][C:4]([NH:6][C:7]1[CH:15]=[C:14]2[C:10]([C:11]([CH3:18])([CH3:17])[C:12](=[O:16])[NH:13]2)=[CH:9][C:8]=1[N+:19]([O-])=O)=O.[H][H]>[Pd].C(O)C>[CH3:1][O:2][CH2:3][C:4]1[NH:6][C:7]2[CH:15]=[C:14]3[NH:13][C:12](=[O:16])[C:11]([CH3:18])([CH3:17])[C:10]3=[CH:9][C:8]=2[N:19]=1

Participants

5

Reactant 2

HCID 20149318HCID 20149318, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 178494634HCID 178494634, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Analogously to Example 5, 1.6 g. (5.4 mmole) 6-methoxymethylcarbonylamino-5-nitro-3,3-dimethylindolin-2-one are dissolved in 160 ml. ethanol and hydrogenated in the presence of 0.8 g. 10% palladium on charcoal at normal pressure and ambient temperature. After 360 ml. of hydrogen have been taken up, the catalyst is filtered off with suction and the filtrate is evaporated to dryness in a vacuum. The residue is purified over a silica gel column (elution agent: dichloromethane/methanol 95:5 v/v). The appropriate fractions are evaporated to dryness and the residue is recrystallised from isopropanol. There are obtained 800 mg. (60% of theory) of the title compound; m.p. 203°-205° C.

Workup

  1. customat normal pressure and ambient temperature
  2. filtrationthe catalyst is filtered off with suction
  3. customthe filtrate is evaporated to dryness in a vacuum
  4. customThe residue is purified over a silica gel column (elution agent: dichloromethane/methanol 95:5 v/v)
  5. customThe appropriate fractions are evaporated to dryness
  6. customthe residue is recrystallised from isopropanol
  7. customThere are obtained 800 mg

Sources & evidence

ORD record
ord-611f9ef3f0554365a097ba70b72330cb
Source dataset
uspto-grants-1988_03
Patent number
US04730003

Reaction notes

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