Ethanol → Ethyl 2-chloroisonicotinate
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][N:10]=1)[C:5]([OH:7])=[O:6].[CH2:11](O)[CH3:12].OS(O)(=O)=O>C(OCC)(=O)C>[CH2:11]([O:6][C:5](=[O:7])[C:4]1[CH:8]=[CH:9][N:10]=[C:2]([Cl:1])[CH:3]=1)[CH3:12]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
The mixture of 2-chloro-isonicotinic acid (16.8 g, 0.107 mol), 100 mL absolute ethanol and concentrate H2SO4 (3.28 mL, 0.118 mol) was refluxed under nitrogen for 15 h. After all starting material converted, the mixture was cool down to rt, and vacuumed down all ethanol. The resulted mixture was diluted with 250 mL ethyl acetate, washed with sat. NaHCO3, dried over anhydrous Na2SO4. Purified by a short column, the 2-chloro-isonicotinic acid ethyl ester was obtained in as a pale yellow liquid. MS (ES+): 186 (M+H)+.
Workup
- temperaturewas refluxed under nitrogen for 15 h
- washwashed with sat. NaHCO3
- dry with materialdried over anhydrous Na2SO4
- customPurified by a short column
Sources & evidence
- ORD record
- ord-9810df5ffbfb4cdfb59ada94e8985ce3
- Source dataset
- uspto-grants-2009_09
- Patent number
- US07582631B2
Reaction notes
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