Ethanol → Ethyl 2,5-dichloronicotinate
Reaction equation
[Cl:1][C:2]1[N:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH2:12](O)[CH3:13].S(=O)(=O)(O)O.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[N:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:3]=1[C:4]([O:6][CH2:12][CH3:13])=[O:5]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 130 °C
Procedure
To a solution of 2,5-dichloronicotinic acid (30 g, 0.16 mol) in toluene (100 ml) was added ethanol (50 ml) and cone, sulfuric acid (1 ml). The reaction mixture was heated at 130° C. for 3 days with stirring. Then the reaction mixture was cooled and poured into sat. sodium bicarbonate solution. The whole mixture was extracted with ethyl acetate. The organic phase was washed with brine, dried (sodium sulfate), and concentrated to afford 34 g (quant.) of title compound:
Workup
- temperatureThen the reaction mixture was cooled
- extractionThe whole mixture was extracted with ethyl acetate
- washThe organic phase was washed with brine
- dry with materialdried (sodium sulfate)
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-7a57fb49b780498c840bae7fae7a2233
- Source dataset
- uspto-grants-2011_12
- Patent number
- US08084476B2
Reaction notes
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