Ethanol → HCID 22012981, compound

HRID 378702Notes

Reaction equation

HRID 378702 reaction equation
O[N:2]=[C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[NH:5][C:4]1=[O:12].[CH2:13]([OH:15])[CH3:14]>[Rh]>[CH3:3][C:11]1[CH:6]=[CH:7][C:8]([CH2:14][C:13]([NH:2][CH:3]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[NH:5][C:4]2=[O:12])=[O:15])=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 702EthanolHCID 178517103HCID 178517103, compound

Product 1

HCID 22012981HCID 22012981, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 23948RhodiumCatalyst

Procedure

A solution of 4.86 g of 3-(hydroxyimino)indolin-2-one and 100 mg of 5% Rh/C in 300 ml of ethanol was stirred at room temperature under a hydrogen atmosphere for 1 day. The reaction mixture was filtered through Cerite, and the filtrate was concentrated. The concentrate was dissolved in 50 ml of N,N-dimethylformamide, and 5.15 g of dicyclohexyl-carbodiimide, 3.83 g of 1-hydroxybenzotriazole, and 3.75 g of p-tolylacetic acid were added thereto successively. The mixture was stirred at the same temperature for 12 hours, whereupon a precipitate formed. The precipitate was filtered off, and the filtrate was concentrated. The concentrate was diluted with ethyl acetate and washed successively with dilute hydrochloric acid and saturated aqueous sodium hydrogencarbonate. The organic layer was dried over anhydrous sodium sulfate and concentrated. The residue was purified by silica gel column chromatography (chloroform/methanol=40/1) to afford 1.01 g (18%) of the title compound.

Workup

  1. filtrationThe reaction mixture was filtered through Cerite
  2. concentrationthe filtrate was concentrated
  3. dissolutionThe concentrate was dissolved in 50 ml of N,N-dimethylformamide
  4. addition5.15 g of dicyclohexyl-carbodiimide, 3.83 g of 1-hydroxybenzotriazole, and 3.75 g of p-tolylacetic acid were added
  5. customformed
  6. filtrationThe precipitate was filtered off
  7. concentrationthe filtrate was concentrated
  8. additionThe concentrate was diluted with ethyl acetate
  9. washwashed successively with dilute hydrochloric acid and saturated aqueous sodium hydrogencarbonate
  10. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  11. concentrationconcentrated
  12. customThe residue was purified by silica gel column chromatography (chloroform/methanol=40/1)

Sources & evidence

ORD record
ord-2827e4ef4f004cf88f23eb1b11f0945d
Source dataset
uspto-grants-2000_02
Patent number
US06031111

Reaction notes

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