Water → HCID 15413204, compound

HRID 724746Notes

Reaction equation

HRID 724746 reaction equation
O.[O:2]=[C:3]1[CH2:11][CH2:10][CH2:9][C:8]2[N:7]([CH2:12][CH2:13][OH:14])[CH:6]=[CH:5][C:4]1=2>[Pd].COCCOCCOC.ClCCl>[OH:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH:5]=[CH:6][N:7]2[CH2:12][CH2:13][OH:14]

Participants

6

Reactant 2

HCID 962WaterHCID 19598464HCID 19598464, compound

Product 1

HCID 15413204HCID 15413204, compoundYield 44.5%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 6344DichloromethaneSolventHCID 8150DiglymeSolvent

Conditions

Temperature
162 °C

Procedure

15 g of palladium on carbon at 5% by weight and containing 50% of water were added to a solution of 25 g of 4-oxo-4,5,6,7-tetrahydro-1-N-(β-hydroxyethyl)indole, obtained in the preceding stage, in 300 cm3 of diglyme. The temperature of the mixture was raised and maintained at 162° C. for 10 hours. The mixture was then allowed to return to a temperature of 40° C. and then the catalyst was filtered off. The solvents were then removed under vacuum until 21.4 g of crude product were obtained which were taken up in a mixture of 30 cm3 of dichloromethane and 200 cm3 of petroleum ether. The crystals obtained were drained, washed with petroleum ether and then dried under vacuum over phosphorus pentoxide. 11 g of 4-hydroxy-1-N-(β-hydroxyethyl)indole were obtained whose elemental analysis, calculated for C10H11NO2, was:

Workup

  1. temperatureThe temperature of the mixture was raised
  2. customto return to a temperature of 40° C.
  3. filtrationthe catalyst was filtered off
  4. customThe solvents were then removed under vacuum until 21.4 g of crude product
  5. customwere obtained which
  6. customThe crystals obtained
  7. washwashed with petroleum ether
  8. dry with materialdried under vacuum over phosphorus pentoxide

Sources & evidence

ORD record
ord-f7c9adf954f74ae482920a8d1901b114
Source dataset
uspto-grants-1998_01
Patent number
US05704948

Reaction notes

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