Sulfuric Acid → Methyl 2-acetylpyridine-4-carboxylate
Reaction equation
S(=O)(=O)(O)O.C[Si]([C:10]#[C:11][C:12]1[CH:13]=[C:14]([CH:19]=[CH:20][N:21]=1)[C:15]([O:17][CH3:18])=[O:16])(C)C.C(=O)(O)[O-:23].[Na+]>O1CCCC1.C(OCC)C.C([O-])(=O)C.[Hg+]>[C:11]([C:12]1[CH:13]=[C:14]([CH:19]=[CH:20][N:21]=1)[C:15]([O:17][CH3:18])=[O:16])(=[O:23])[CH3:10]Participants
7
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 50 °C
Procedure
Concentrated sulfuric acid (60 mL, 1.1 mol) was added to a suspension of methyl 2-((trimethylsilyl)ethynyl)isonicotinate (127 g, 0.54 mol) in tetrahydrofuran (600 mL) and mercury acetate (51.5 g, 0.16 mol). The suspension was stirred for 3 hours at 50° C. and kept overnight. The reaction mixture was diluted with diethyl ether (1.5 L) and the sulfuric acid was neutralized with saturated sodium bicarbonate (150 g, 1.7 mol). A residue of mercury salts was separated by filtration. The ether solution was washed with water and dried over sodium sulfate. The solvent was removed to give methyl 2-acetylisonicotinate as an oil that was directly used in the next step.
Workup
- waitkept overnight
- customA residue of mercury salts was separated by filtration
- washThe ether solution was washed with water
- dry with materialdried over sodium sulfate
- customThe solvent was removed
Sources & evidence
- ORD record
- ord-f4da849520ff4d36ab62cc2ebbbbac09
- Source dataset
- uspto-grants-2012_10
- Patent number
- US08288405B2
Reaction notes
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