Methanol → Methyl 2-chloro-5-fluoronicotinate
Reaction equation
[Cl:1][C:2]1[N:10]=[CH:9][C:8]([F:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].S(=O)(=O)(O)O.[OH-].[Na+].[CH3:19]O>>[Cl:1][C:2]1[N:10]=[CH:9][C:8]([F:11])=[CH:7][C:3]=1[C:4]([O:6][CH3:19])=[O:5]Participants
5
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 2-chloro-5-fluoronicotinic acid (5.2 g, 30 mmol) in methanol (20 ml) was added cone, sulfuric acid (0.5 ml) and the reaction mixture was stirred at reflux for 30 hours. The reaction mixture was cooled to 0° C. and 0.5 N sodium hydroxide solution was added to the mixture. The whole was extracted with diethylether. The organic phase was washed with brine, dried (sodium sulfate), and concentrated to afford 3.2 g (25%) of the title compound:
Workup
- temperatureat reflux for 30 hours
- extractionThe whole was extracted with diethylether
- washThe organic phase was washed with brine
- dry with materialdried (sodium sulfate)
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-a769b96ebc704cbe967caff54181e0ee
- Source dataset
- uspto-grants-2011_12
- Patent number
- US08084476B2
Reaction notes
Loading…