Methanol → HCID 18688761, compound

HRID 355290Notes

Reaction equation

HRID 355290 reaction equation
[ClH:1].[C:2]([CH2:5][CH2:6][N:7]1[CH:12]=[CH:11][C:10](=[O:13])[C:9]([OH:14])=[C:8]1[CH3:15])([OH:4])=[O:3].[CH3:16]O>Cl>[ClH:1].[OH:14][C:9]1[C:10](=[O:13])[CH:11]=[CH:12][N:7]([CH2:6][CH2:5][C:2]([O:4][CH3:16])=[O:3])[C:8]=1[CH3:15]

Participants

4

Reactant 2

HCID 887MethanolHCID 18688772HCID 18688772, compound

Product 1

HCID 18688761HCID 18688761, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

1-(2'-carboxyethyl)-3-hydroxy-2-methylpyrid-4-one hydrochloride (2 g) prepared as described under Example 17, is dissolved in methanol saturated with hydrogen chloride and the solution is refluxed for 3 hours. Rotary evaporation of the solution yields a white solid which on recrystallisation from methanol gives 3-hydroxy-1-(2'-methoxycarbonylethyl)-2-methylpyrid-4-one hydrochloride in 80% yield m.p. 140°-141° C., νmax 1545, 1595, 1645, 1730, 1750 cm-1, δ(d6DMSO), 2.45 (s, 3H), 2.85 (t, 2H), 3.5 (s, 3H), 4.45 (t, 2H), 7.30 (d, 1H), 8.15 (d, 1H).

Workup

  1. temperaturethe solution is refluxed for 3 hours
  2. customRotary evaporation of the solution
  3. customyields a white solid which
  4. customon recrystallisation from methanol

Sources & evidence

ORD record
ord-fc918976911d4a3b92698bcb4cd50d38
Source dataset
uspto-grants-1998_11
Patent number
USRE035948

Reaction notes

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