Ethanol → Ethyl 2-chloroisonicotinate

HRID 729534Notes

Reaction equation

HRID 729534 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

HCID 702Ethanol2×HCID 1118Sulfuric AcidHCID 2369852-Chloroisonicotinic acid

Product 1

HCID 2762942Ethyl 2-chloroisonicotinate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

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

  1. temperaturewas refluxed under nitrogen for 15 h
  2. washwashed with sat. NaHCO3
  3. dry with materialdried over anhydrous Na2SO4
  4. 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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