Water → HCID 15413204, compound

HRID 1291936Notes

Reaction equation

HRID 1291936 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>COCCOCCOC.ClCCl.[Pd]>[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 5% by weight palladium-on-charcoal, 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 brought to and maintained at 162° C. for 10 hours. The mixture was then allowed to return to a temperature of 40° C. and the catalyst was then 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 filtered off, washed with petroleum ether and then dried under vacuum over phosphorus pentoxide. 11 g of 4-hydroxy-1-N-(β-hydroxyethyl)indole were obtained, the melting point of which was 109° C.

Workup

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

Sources & evidence

ORD record
ord-4ae2d011873243ee833937bf3c5618d7
Source dataset
uspto-grants-1998_05
Patent number
US05755829

Reaction notes

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