Ethanol → Ethyl 3-chloroisonicotinate
Reaction equation
[Cl:1][C:2]1[CH:10]=[N:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH3:11][CH2:12]O>OS(O)(=O)=O>[CH2:11]([O:5][C:4](=[O:6])[C:3]1[CH:7]=[CH:8][N:9]=[CH:10][C:2]=1[Cl:1])[CH3:12]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 3-chloroisonicotinic acid (18.6 mmol) in 120 mL EtOH and 3 mL conc. H2SO4 was heated to reflux overnight. The mixture was concentrated in vacuo, redissolved in aq. NaHCO3 solution and extracted with EtOAc (2×). The combined organic layers were dried over MgSO4 and concentrated in vacuo to give the desired product as yellow oil;
Workup
- temperatureto reflux overnight
- concentrationThe mixture was concentrated in vacuo
- dissolutionredissolved in aq. NaHCO3 solution
- extractionextracted with EtOAc (2×)
- dry with materialThe combined organic layers were dried over MgSO4
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-705167690877422d912cde74f65b8ce1
- Source dataset
- uspto-grants-2015_12
- Patent number
- US09221832B2
Reaction notes
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