Sodium Hydroxide → 3-ethyl-6-methyl-1H-pyridin-2-one

HRID 1921305Notes

Reaction equation

HRID 1921305 reaction equation
[CH2:1]([C:3]1[C:4](N)=[N:5][C:6]([CH3:9])=[CH:7][CH:8]=1)[CH3:2].N([O-])=[O:12].[Na+].[OH-].[Na+]>S(=O)(=O)(O)O.O>[CH2:1]([C:3]1[C:4](=[O:12])[NH:5][C:6]([CH3:9])=[CH:7][CH:8]=1)[CH3:2]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 30163113-Ethyl-6-methylpyridin-2-amineHCID 23668193Sodium Nitrite

Product 1

HCID 27978763-ethyl-6-methyl-1H-pyridin-2-oneYield 87%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Procedure

A solution of 3-ethyl-6-methyl(pyridin-2-yl)amine (also see Reimlinger, H. et al. Chem. Ber., 109, 118-124 (1976); Sawyer, J. R. H.; Wibberley, D. G. J. Chem. Soc (Perkin 1), 113801143 (1973); Childs, R. F.; Johnson, A. W. Chem. Ind. (London), 542 (1964)) (41.2 g, 0.4 mol) in sulfuric acid (817 mL) is chilled in an ice bath. To this solution is added a solution of sodium nitrite (23.81 g, 0.345 mol) in H2O (200 mL). The resulting mixture is stirred at ambient temperature for 20 hr. The mixture is brought to pH 9.0 by addition of 3N sodium hydroxide (370 mL) and extracted with ethyl acetate (9×200 mL). The combined organic extract is washed with brine (300 mL), dried, filtered and concentrated. The residue is crystallized from heptane (300 mL) to afford 3-ethyl-6-methyl-1H-pyridin-2-one (also disclosed by Mistryukov, E. A. et al. Izv. Akad. Nauk SSR 512-519 (1964); Chem. Abstr. 64, 90713) (35.78 g, 87% yield) as a white, crystalline solid. The resulting product exhibited characteristic 1H NMR spectrum consistent with that reported in the literature.

Workup

  1. extractionextracted with ethyl acetate (9×200 mL)
  2. extractionThe combined organic extract
  3. washis washed with brine (300 mL)
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue is crystallized from heptane (300 mL)

Sources & evidence

ORD record
ord-63f2416904c442018cfb16c188cbbced
Source dataset
uspto-grants-2012_05
Patent number
US08173682B2

Reaction notes

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