Hydrochloric Acid → 5,6-Dimethyl-2-pyridone

HRID 2235970Notes

Reaction equation

HRID 2235970 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4](C#N)[C:5](=[O:9])[NH:6][C:7]=1[CH3:8].Cl.[OH-].[Na+]>O>[CH3:1][C:2]1[CH:3]=[CH:4][C:5](=[O:9])[NH:6][C:7]=1[CH3:8]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 5905325,6-Dimethyl-2-oxo-1,2-dihydropyridine-3-carbonitrile

Product 1

HCID 1197855,6-Dimethyl-2-pyridoneYield 48.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
175 °C

Procedure

A 100 mL Parr reactor was charged with 5,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinecarbonitrile (Example 475, 3.00 g, 20.3 mmol), concentrated hydrochloric acid (18 mL), and water (18 mL). The reactor was slowly heated to 175° C. for 9 h and then cooled to rt. The solution was basified with 1N NaOH in water and was extracted with EtOAc. The combined organic phases were dried (MgSO4), filtered, and concentrated in vacuo, yielding the title compound (1.21 g, 48%) as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ 11.36 (bs, 1H), 7.18 (d, 1H), 6.04 (d, 1H), 2.10 (s, 3H), 1.93 (s, 3H).

Workup

  1. temperaturecooled to rt
  2. extractionwas extracted with EtOAc
  3. dry with materialThe combined organic phases were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c7cd80e8c12b468e932063ace0fb364f
Source dataset
uspto-grants-2010_05
Patent number
US07714004B2

Reaction notes

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