Solketal → HCID 10488217, compound

HRID 566864Notes

Reaction equation

HRID 566864 reaction equation
[CH3:1][C:2]1[NH:3][CH:4]=[CH:5][C:6](=[O:9])[C:7]=1[OH:8].CC1(C)[O:15][CH:14]([CH2:16]O)[CH2:13][O:12]1.CC1NC=CC(=O)C=1OCC1C=CC=CC=1>OCC(CO)O>[CH2:16]([N:3]1[CH:4]=[CH:5][C:6](=[O:9])[C:7]([OH:8])=[C:2]1[CH3:1])[CH:14]([CH2:13][OH:12])[OH:15]

Participants

5

Reactant 3

HCID 7528Solketal2×HCID 3238144-Pyridinone,3-OH-2-Me2×HCID 27264163-(BENZYLOXY)-2-METHYL-4(1H)-PYRIDINONE

Product 1

HCID 10488217HCID 10488217, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 753GlycerolSolvent2×

Procedure

The 2-methyl-3-hydroxypyridine-4(1H)-one of glycerol is prepared starting from the 2-methyl-3-hydroxypyridine-4(1H)-one of solketal according to the method described in example 15. The extraction and purification protocol is the following: filtration of the catalyst, addition of water, followed by elimination of the organic solvent, lyophilization, retake-up of the residue by an organic solvent, neutralization using Dowex OH− resin, filtration, and finally evaporation of the solvent. Starting from 1.00 g (3.04 mmol) of 2-methyl-3-benzyloxypyridine-4(1H)-one of solketal, 790 mg (2.73 mmol) of 2-methyl-3-hydroxypyridine-4(1H)-one of glycerol is isolated, which is pure at chromatographic and NMR analyses. Yield: 90%.

Workup

  1. extractionThe extraction and purification protocol
  2. filtrationfiltration of the catalyst, addition of water
  3. filtrationDowex OH− resin, filtration, and finally evaporation of the solvent
  4. customis isolated

Sources & evidence

ORD record
ord-3e2de0cbf3184df9865b8bd270a227a7
Source dataset
uspto-grants-2001_01
Patent number
US06177409B1

Reaction notes

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