Water → Methyl 1-cyclohexyl-6-oxo-1,6-dihydropyridine-3-carboxylate

HRID 1921280Notes

Reaction equation

HRID 1921280 reaction equation
CO/[CH:3]=[C:4](\[C:11]([O:13][CH3:14])=[O:12])/[CH:5]=[CH:6]/[C:7]([O:9]C)=O.[CH:15]1([NH2:21])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1.O>CN(C=O)C>[CH:15]1([N:21]2[C:7](=[O:9])[CH:6]=[CH:5][C:4]([C:11]([O:13][CH3:14])=[O:12])=[CH:3]2)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

5

Reactant 3

HCID 962WaterHCID 7965CyclohexylamineHCID 13794930HCID 13794930, compound

Product 1

HCID 15946190Methyl 1-cyclohexyl-6-oxo-1,6-dihydropyridine-3-carboxylateYield 36%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of dimethyl (2E,4Z)-4-(methoxymethylene)-2-pentenedioate (1.23 g) in DMF (30 mL) was added cyclohexanamine (670 mg) at 0° C., and the mixture was stirred at the same temperature for 30 min under a nitrogen atmosphere. The reaction mixture was heated to reflux for 5 hr. The mixture was cooled with an ice-water bath and poured into water (100 mL). The resulted mixture was extracted with EtOAc (100 mL×2), and the organic phases were combined, washed with brine two times, dried over MgSO4, filtered and evaporated in vacuo. The residue was purified by silica gel column chromatography eluting with EtOAc-hexane (1:2-1:1) to give methyl 1-cyclohexyl-6-oxo-1,6-dihydro-3-pyridinecarboxylate (520 mg).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 5 hr
  3. temperatureThe mixture was cooled with an ice-water bath
  4. extractionThe resulted mixture was extracted with EtOAc (100 mL×2)
  5. washwashed with brine two times
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customevaporated in vacuo
  9. customThe residue was purified by silica gel column chromatography
  10. washeluting with EtOAc-hexane (1:2-1:1)

Sources & evidence

ORD record
ord-497324d352824a2e924aa2e22acce240
Source dataset
uspto-grants-2012_05
Patent number
US08173684B2

Reaction notes

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