Water → Methyl 1-cyclohexyl-6-oxo-1,6-dihydro-3-pyridinecarboxylate

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

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).