Hydrochloric Acid → Methyl 1-(2-methylphenyl)-2-oxo-1,2-dihydropyridine-3-carboxylate

HRID 2095795Notes

Reaction equation

HRID 2095795 reaction equation
O=[C:2]1[C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=[CH:4][O:3]1.[CH3:12][C:13]1[CH:19]=[CH:18][CH:17]=[CH:16][C:14]=1[NH2:15].Cl.C(N=C=NCCCN(C)C)C.Cl>O1CCCC1.CN(C)C=O.CN(C)C1C=CN=CC=1>[CH3:12][C:13]1[CH:19]=[CH:18][CH:17]=[CH:16][C:14]=1[N:15]1[CH:4]=[CH:5][CH:6]=[C:7]([C:8]([O:10][CH3:11])=[O:9])[C:2]1=[O:3]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 7242O-ToluidineHCID 117704Methyl 2-oxo-2H-pyran-3-carboxylateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 58158571Methyl 1-(2-methylphenyl)-2-oxo-1,2-dihydropyridine-3-carboxylateYield 19%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 2-oxo-2H-pyran-3-carboxylate (3 g, 19.5 mmol) in tetrahydrofuran (30 mL) and N,N-dimethylformamide (10 mL) was added 2-methylaniline (2.09 g, 19.5 mmol), and the mixture was stirred at room temperature for 7 hr. 4-Dimethylaminopyridine (119 mg, 0.974 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (4.48 g, 23.4 mmol) were added to the reaction mixture, and the mixture was further stirred at room temperature for 17 hr. 1N Hydrochloric acid was added to the reaction solution, and the mixture was extracted 3 times with ethyl acetate. The combined organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and filtered, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (NH silica gel, ethyl acetate/hexane=1/1) to give the title compound (882 mg, 19%) as yellow crystals.

Workup

  1. stirringthe mixture was further stirred at room temperature for 17 hr
  2. extractionthe mixture was extracted 3 times with ethyl acetate
  3. washThe combined organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customthe solvent was evaporated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography (NH silica gel, ethyl acetate/hexane=1/1)

Sources & evidence

ORD record
ord-f2d6eedbb14c49e18164cd52a049e608
Source dataset
uspto-grants-2013_05
Patent number
US08445509B2

Reaction notes

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