Acetic Acid → HCID 14950465, compound

HRID 654365Notes

Reaction equation

HRID 654365 reaction equation
C(Cl)(Cl)Cl.[CH3:5][C:6]1[NH:7][C:8]([CH3:13])=[CH:9][C:10](=[O:12])[CH:11]=1.[C:14](O)(=[O:16])C>[OH-].[Na+]>[CH3:5][C:6]1[NH:7][C:8]([CH3:13])=[CH:9][C:10](=[O:12])[C:11]=1[CH:14]=[O:16]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 6212ChloroformHCID 836092,6-Dimethylpyridin-4(1H)-one

Product 1

HCID 14950465HCID 14950465, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

Chloroform (12 ml) was added in 1 ml portions over a period of 2 hours to a refluxing solution of 2,6-dimethyl-4-(1H)-pyridone (6.2 g) in 4M aqueous sodium hydroxide (112 ml). The solution was heated under reflux for 6 hours, cooled and acidified to pH 6 with acetic acid. Volatile material was removed by evaporation and the residue was extracted with methanol (3×100 ml). The extracts were concentrated and the residue was purified by flash chromatography, eluting with methanol/dichloromethane (1:9 v/v), to give 2,6-dimethyl-3-formyl-4(1H)-pyridone (B) (2.1 g) as a solid, m.p. >100° C. (decomposition); NMR (d6 -DMSO): 2.2(s,3H), 2.5(s,3H), 6.1(s,1H), 10.25(s,1H).

Workup

  1. temperatureThe solution was heated
  2. temperatureunder reflux for 6 hours
  3. temperaturecooled
  4. customVolatile material was removed by evaporation
  5. extractionthe residue was extracted with methanol (3×100 ml)
  6. concentrationThe extracts were concentrated
  7. customthe residue was purified by flash chromatography
  8. washeluting with methanol/dichloromethane (1:9 v/v)

Sources & evidence

ORD record
ord-17bbf33cfd7347a08759e925c6aab94e
Source dataset
uspto-grants-1992_07
Patent number
US05130318

Reaction notes

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