Methanol → Methyl 3-Hydroxy-2-pyridinecarboxylate
Reaction equation
[OH:1][C:2]1[C:3]([C:8]([OH:10])=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=1.OS(O)(=O)=O.[CH3:16]O>>[CH3:16][O:9][C:8]([C:3]1[C:2]([OH:1])=[CH:7][CH:6]=[CH:5][N:4]=1)=[O:10]Participants
4
Conditions
- Temperature
- 64 °C
Procedure
In a 500 mL round-bottom flask fitted with condenser and magnetic stirrer were placed MeOH (250 mL), 3-hydroxypyridine-2-carboxylic acid (10.0 g, 71.9 mmol) and concentrated H2SO4 (3 mL). The reaction mixture was heated at 64° C. for 24 hs. The reaction mixture was cooled to rt. The solvent was removed under reduced pressure; the residue was partitioned between EtOAc (150 mL) and water (20 mL). Solid sodium carbonate was added to adjust pH to 6. The organic layer was separated, dried over Na2SO4, concentrated to give 3.5 g of crude 3-hydroxypyridine-2-carboxylic acid methyl ester (32%).
Workup
- customIn a 500 mL round-bottom flask fitted with condenser and magnetic stirrer
- temperatureThe reaction mixture was cooled to rt
- customThe solvent was removed under reduced pressure
- customthe residue was partitioned between EtOAc (150 mL) and water (20 mL)
- additionSolid sodium carbonate was added
- customThe organic layer was separated
- dry with materialdried over Na2SO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-911279747639478da7adbd2f05bbaf4f
- Source dataset
- uspto-grants-2012_01
- Patent number
- US08093273B2
Reaction notes
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