2,6-Dimethylaniline → Methyl 1-(2,6-dimethylphenyl)-6-oxo-1,6-dihydropyridine-3-carboxylate

HRID 2426968Notes

Reaction equation

HRID 2426968 reaction equation
[H-].[Na+].[CH3:3][C:4]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[C:5]=1[NH2:6].[CH3:12][O:13][C:14]([C:16]1[CH:22]=[CH:21][C:19](=O)[O:18][CH:17]=1)=[O:15].[Cl-].[NH4+]>O1CCCC1>[CH3:3][C:4]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[C:5]=1[N:6]1[C:19](=[O:18])[CH:21]=[CH:22][C:16]([C:14]([O:13][CH3:12])=[O:15])=[CH:17]1

Participants

6

Reactant 4

HCID 68962,6-DimethylanilineHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 80113Methyl coumalate

Product 1

HCID 67251224Methyl 1-(2,6-dimethylphenyl)-6-oxo-1,6-dihydropyridine-3-carboxylateYield 33.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a suspended solution of sodium hydride (60% in oil, 14.5 g) in tetrahydrofuran (240 mL) were added 2,6-dimethylaniline (29.3 g) and methyl coumalate (18.6 g) and the mixture was stirred at 60° C. for 4 hours. To the reaction mixture was added an aqueous solution of ammonium chloride and the mixture was extracted with ethyl acetate. The obtained organic layer was dried and concentrated. The obtained residue was purified by column chromatography on silica gel (hexane:ethyl acetate=3:2) to give the title compound (10.4 g) having the following physical data.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. customThe obtained organic layer was dried
  3. concentrationconcentrated
  4. customThe obtained residue was purified by column chromatography on silica gel (hexane:ethyl acetate=3:2)

Sources & evidence

ORD record
ord-15c66d7406d3458b927283816da31e6b
Source dataset
uspto-grants-2011_06
Patent number
US07968572B2

Reaction notes

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