Sodium ethoxide → 1,6-Naphthyridin-2(1H)-one, 5,8-dimethyl-
Reaction equation
[NH2:1][C:2]1[C:7]([CH3:8])=[CH:6][N:5]=[C:4]([CH3:9])[C:3]=1/[CH:10]=[CH:11]/[C:12]([O:14]CC)=O.C([O-])C.[Na+]>C(O)C>[CH3:9][C:4]1[N:5]=[CH:6][C:7]([CH3:8])=[C:2]2[C:3]=1[CH:10]=[CH:11][C:12](=[O:14])[NH:1]2Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
A mixture of (E)-ethyl 3-(4-amino-2,5-dimethylpyridin-3-yl)acrylate (5 g, 22.7 mmol) and sodium ethanolate (6.2 g, 91 mmol) in ethanol (100 mL) was heated to 80° C. for 2 h. The reaction mixture was concentrated and diluted with water (50 mL). The aqueous phase was extracted with EtOAc (100 mL×3), and the combined organic layers were washed with saturated sodium chloride solution, dried with sodium sulfate, and concentrated to give 2.3 g of the product as a yellow solid. MS (ESI): m/z 175.1 [M+H]+.
Workup
- concentrationThe reaction mixture was concentrated
- additiondiluted with water (50 mL)
- extractionThe aqueous phase was extracted with EtOAc (100 mL×3)
- washthe combined organic layers were washed with saturated sodium chloride solution
- dry with materialdried with sodium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-9a749d6ff6294f38877a5ad4a12e0ff9
- Source dataset
- uspto-grants-2015_03
- Patent number
- US08969349B2
Reaction notes
Loading…