Ethanol → Ethyl 2,6-dichloronicotinate

HRID 1664332Notes

Reaction equation

HRID 1664332 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].OS(O)(=O)=O.[CH3:17][CH2:18]O>>[Cl:1][C:2]1[N:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4]([O:6][CH2:17][CH3:18])=[O:5]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 8540472,6-Dichloronicotinic acid

Product 1

HCID 12263987Ethyl 2,6-dichloronicotinateYield 85.2%

Procedure

Esterification of 2,6-dichloronicotinic acid (25.5 g, 0.1328 mmol) in EtOH (200 proof, 200 mL) catalyzed with 96% H2SO4 (1.7 g) at refluxing temperature for 40 h under N2 gave the desired ethyl 2,6-dichloronicotinate as grey solid (24.89 g, 0.1131 mmol, yield 85.2%) after a normal work-up.

Workup

  1. temperatureat refluxing temperature for 40 h under N2

Sources & evidence

ORD record
ord-637de04ddf964fe9b13d8cbb7d700a01
Source dataset
uspto-grants-2011_10
Patent number
US08039450B2

Reaction notes

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