Hydrochloric Acid → Ethyl 2-(6-methoxypyridin-2-YL)acetate
Reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7]([CH:9](C(OCC)=O)[C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:6]=[CH:5][CH:4]=1.Cl>C(O)C>[CH3:1][O:2][C:3]1[N:8]=[C:7]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:6]=[CH:5][CH:4]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 65 °C
Procedure
A solution of diethyl 2-(6-methoxypyridin-2-yl)malonate (1.0 g, 3.74 mmol) and hydrochloric acid (1 M) (20 mL, 20.0 mmol) in ethanol (10 mL) was heated at 65° C. overnight. The solvent was removed under reduced pressure. The residue was dissolved in ethanol (15 mL) and hydrochloric acid (conc.) (0.5 mL, 6.00 mmol) was added. The reaction mixture was heated at 65° C. for 4 h. The solvent was removed under reduced pressure. Ethyl acetate and saturated NaHCO3 aqueous solution were added. The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were dried (Na2SO4) and concentrated to give the product. Yield: 0.69 g (94%).
Workup
- customThe solvent was removed under reduced pressure
- dissolutionThe residue was dissolved in ethanol (15 mL)
- customThe solvent was removed under reduced pressure
- additionEthyl acetate and saturated NaHCO3 aqueous solution were added
- customThe organic layer was separated
- extractionthe aqueous layer was extracted with ethyl acetate
- dry with materialThe combined organic layers were dried (Na2SO4)
- concentrationconcentrated
- customto give the product
Sources & evidence
- ORD record
- ord-84a06a4b777748848d4e1887319362c8
- Source dataset
- uspto-grants-2014_10
- Patent number
- US08859534B2
Reaction notes
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