HCID 20149329, compound → HCID 178439845, compound

HRID 568810Notes

Reaction equation

HRID 568810 reaction equation
[CH2:1]([C:4]([NH:6][C:7]1[CH:15]=[C:14]2[C:10]([C:11]([C:18]([O:20][CH2:21][CH3:22])=[O:19])([CH3:17])[C:12](=[O:16])[NH:13]2)=[CH:9][C:8]=1[N+:23]([O-])=O)=O)[CH2:2][CH3:3].[H][H]>[Pd].C(O)C>[CH2:1]([C:4]1[NH:6][C:7]2[CH:15]=[C:14]3[NH:13][C:12](=[O:16])[C:11]([C:18]([O:20][CH2:21][CH3:22])=[O:19])([CH3:17])[C:10]3=[CH:9][C:8]=2[N:23]=1)[CH2:2][CH3:3]

Participants

5

Reactant 2

HCID 20149329HCID 20149329, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 178439845HCID 178439845, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

Analogously to Example 5, 1.40 g. (4.0 mmole) 6-propylcarbonylamino-5-nitro-3-ethoxycarbonyl-3-methylindolin-2-one is suspended in 140 ml. ethanol and hydrogenated in the presence of 0.1 g. 10% palladium on charcoal at normal pressure and ambient temperature. After 270 ml. of hydrogen have been taken up, the catalyst is filtered off with suction and the filtrate is evaporated to dryness. The residue is stirred for 1 hour at 60° C. in 10 ml. glacial acetic acid, the glacial acetic acid is distilled off and the residue is taken up in water and neutralised with 2N aqueous sodium hydroxide solution. The mixture is shaken out three times with dichloromethane and the combined dichloromethane phases are dried over anhydrous sodium sulphate, filtered and the filtrate evaporated to dryness. After crystallisation of the residue from isopropanol, there is obtained 0.4 g. (33% of theory) of the title compound; m.p. 258°-261° C.

Workup

  1. customat normal pressure and ambient temperature
  2. filtrationthe catalyst is filtered off with suction
  3. customthe filtrate is evaporated to dryness
  4. distillationglacial acetic acid, the glacial acetic acid is distilled off
  5. stirringThe mixture is shaken out three times with dichloromethane
  6. dry with materialthe combined dichloromethane phases are dried over anhydrous sodium sulphate
  7. filtrationfiltered
  8. customthe filtrate evaporated to dryness
  9. customAfter crystallisation of the residue from isopropanol
  10. customthere is obtained 0.4 g

Sources & evidence

ORD record
ord-1c78b986e2814bf98254dc52956e9bc1
Source dataset
uspto-grants-1988_03
Patent number
US04730003

Reaction notes

Loading…