Reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][N:10]=1)[C:5]([OH:7])=[O:6].S(Cl)(Cl)=O.[CH3:15]O>>[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][N:10]=1)[C:5]([O:7][CH3:15])=[O:6]Participants
4
Procedure
To an ice-cooled suspension of 1.32 g (9.62 mmol) of 2-methylisonicotinic acid in 20 mL of MeOH was added 1.47 mL (20.2 mmol) of thionyl chloride. The ice-bath was removed and the reaction was stirred at rt. After 22 h, the MeOH was evaporated and the residue was taken up in H2O. The aqueous mixture was neutralized with saturated NaHCO3, then extracted with Et2O. The organic extracts were washed with saturated NaCl, dried over MgSO4, then filtered through a bed of celite. Eva-poration of solvent in vacuo afforded the title compound as a yellow liquid (0.89 g, 61%): 1H NMR (CDCl3): d 8.66 (d, 1H); 7.72 (s, 1H); 7.64 (d, 1H); 3.98 (s, 3H); 2.64 (s, 3H).
Workup
- customThe ice-bath was removed
- customthe MeOH was evaporated
- extractionextracted with Et2O
- washThe organic extracts were washed with saturated NaCl
- dry with materialdried over MgSO4
- filtrationfiltered through a bed of celite
Sources & evidence
- ORD record
- ord-1f78b6aefe504983ae943362f6cec512
- Source dataset
- uspto-grants-2003_11
- Patent number
- US06645989B2
Linked notes
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