HCID 21474294, compound → HCID 10220846, compound

HRID 2294239Notes

Reaction equation

HRID 2294239 reaction equation
C([O:8][C:9]1[C:14](=[O:15])[CH:13]=[CH:12][N:11]([CH2:16][CH2:17][OH:18])[C:10]=1[CH:19]([OH:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)C1C=CC=CC=1>CO.[Pd]>[OH:8][C:9]1[C:14](=[O:15])[CH:13]=[CH:12][N:11]([CH2:16][CH2:17][OH:18])[C:10]=1[CH:19]([OH:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

4

Reactant 1

HCID 21474294HCID 21474294, compound

Product 1

HCID 10220846HCID 10220846, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

12.37 g of 3-benzyloxy-1-(2-hydroxy-ethyl)-2-(hydroxy-phenyl-methyl)-1H-pyridin-4-one are dissolved in 200 ml of methanol and hydrogenated at room temperature over 1.2 g of palladium on carbon (5%) until 1 mol of H2 per mol of starting material has been taken up. The catalyst is removed by filtration and the filtrate is concentrated to dryness by evaporation using a rotary evaporator. Recrystallisation from methanol yields 3-hydroxy-1-(2-hydroxy-ethyl)-2-(hydroxy-phenyl-methyl)-1H-pyridin-4-one in the form of colourless crystals. M.p.: 198°-200° C.

Workup

  1. customThe catalyst is removed by filtration
  2. concentrationthe filtrate is concentrated to dryness by evaporation
  3. customa rotary evaporator
  4. customRecrystallisation from methanol

Sources & evidence

ORD record
ord-d1381b1993464cc19af7f7c8c4eac603
Source dataset
uspto-grants-1997_11
Patent number
US05688815

Reaction notes

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