Water → 2,6-Difluoro-nicotinic acid methyl ester
Reaction equation
[F:1][C:2]1[N:10]=[C:9]([F:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].S(=O)(=O)(O)O.O.[C:18](=O)([O-])[O-].[K+].[K+]>CO>[CH3:18][O:5][C:4](=[O:6])[C:3]1[CH:7]=[CH:8][C:9]([F:11])=[N:10][C:2]=1[F:1]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To 2,6-difluoro-nicotinic acid (59, 5.60 g, 0.0352 mol) in methanol (60.0 mL) was added concentrated sulfuric acid (1.0 mL, 0.019 mol). The reaction was heated to reflux overnight, then poured into water, basified with 1M potassium carbonate to pH around 9, and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated to give a yellow oil (60, 3.5 g, 57.0%).
Workup
- temperatureThe reaction was heated
- temperatureto reflux overnight
- extractionextracted with ethyl acetate
- dry with materialThe organic layer was dried over anhydrous sodium sulfate
- concentrationconcentrated
- customto give a yellow oil (60, 3.5 g, 57.0%)
Sources & evidence
- ORD record
- ord-457d5bb45a014f8c8eb941300a3b354c
- Source dataset
- uspto-grants-2014_05
- Patent number
- US08722702B2
Reaction notes
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