HCID 21474419, compound → HCID 135576260, compound

HRID 2294246Notes

Reaction equation

HRID 2294246 reaction equation
[C:1]([C:9]1[N:10]([CH2:24][CH2:25][O:26]CC2C=CC=CC=2)[CH:11]=[CH:12][C:13](=[O:23])[C:14]=1[O:15]CC1C=CC=CC=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CO>[C:1]([C:9]1[N:10]([CH2:24][CH2:25][OH:26])[CH:11]=[CH:12][C:13](=[O:23])[C:14]=1[OH:15])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 21474419HCID 21474419, compound

Product 1

HCID 135576260HCID 135576260, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

At room temperature and under normal pressure, 0.95 g of 2-benzoyl-3-benzyloxy-1-(2-benzyloxy-ethyl)-1H-pyridin-4-one is hydrogenated in methanol until 2 mol of H2 per mol of starting material have been taken up. The catalyst is removed and the reaction mixture is concentrated by evaporation using a rotary evaporator. The residue is chromatographed on 20 g of silica gel. A mixture of ethyl acetate and ethanol in a ratio of 95:5 is used as eluant. With fraction sizes of 17 ml, the product in fractions 6-20 is eluted. Recrystallisation from ethanol yields 2-benzoyl-3-hydroxy-1-(2-hydroxy-ethyl)-1H-pyridin-4-one in the form of colourless crystals. M.p.: 195°-200° C.

Workup

  1. customAt room temperature
  2. customThe catalyst is removed
  3. concentrationthe reaction mixture is concentrated by evaporation
  4. customa rotary evaporator
  5. customThe residue is chromatographed on 20 g of silica gel
  6. additionA mixture of ethyl acetate and ethanol in a ratio of 95:5
  7. washWith fraction sizes of 17 ml, the product in fractions 6-20 is eluted
  8. customRecrystallisation from ethanol

Sources & evidence

ORD record
ord-d27b78b8da214bff87be48e12d88ec7b
Source dataset
uspto-grants-1997_11
Patent number
US05688815

Reaction notes

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