Ethanol → HCID 13592494, compound

HRID 1761411Notes

Reaction equation

HRID 1761411 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=[C:12]([CH3:14])[CH3:13].C(O)C.[H][H]>[Pd].O1CCCC1>[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[CH:5]2[CH:12]([CH3:14])[CH3:13]

Participants

6

Reactant 3

HCID 702EthanolHCID 135924925-Hydroxy-3-(propan-2-ylidene)-1,3-dihydro-2H-indol-2-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 13592494HCID 13592494, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

23 g. 5-Hydroxy-3-isopropylideneindolinone are dissolved in 100 ml. ethanol and 150 ml. tetrahydrofuran and hydrogenated in the presence of 1 g. 10% palladium-charcoal at ambient temperature and 1 bar hydrogen pressure. After filtering off the catalyst with suction, the filtrate is distilled off in a vacuum and the residue is triturated with diethyl ether and filtered off with suction. There are obtained 19 g. of the title compound; yield 81% of theory; m.p. 175° C.

Workup

  1. customat ambient temperature
  2. filtrationAfter filtering off the catalyst with suction
  3. distillationthe filtrate is distilled off in a vacuum
  4. customthe residue is triturated with diethyl ether
  5. filtrationfiltered off with suction
  6. customThere are obtained 19 g

Sources & evidence

ORD record
ord-96d6c4a4c9a14edba5c44226dbe47f44
Source dataset
uspto-grants-1989_05
Patent number
US04826847

Reaction notes

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