Ethanol → Ethyl 2-chloroisonicotinate

HRID 1436899Notes

Reaction equation

HRID 1436899 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][N:10]=1)[C:5]([OH:7])=[O:6].C(N1C=CN=C1)(N1[CH:17]=[CH:16]N=C1)=O.C(O)C>O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][N:10]=1)[C:5]([O:7][CH2:16][CH3:17])=[O:6]

Participants

5

Reactant 3

HCID 702EthanolHCID 682631,1'-CarbonyldiimidazoleHCID 2369852-Chloroisonicotinic acid

Product 1

HCID 2762942Ethyl 2-chloroisonicotinateYield 95.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In 400 ml of tetrahydrofuran was dissolved 31.5 g of 2-chloroisonicotinic acid, and 32.5 g of 1,1′-carbonyldiimidazole was added thereto. The mixture was stirred under ice-cooling for an hour. To the solution was added 50 ml of ethanol, and the mixture was stirred at room temperature for 2 hours. The solution was concentrated, and extracted by adding ethyl acetate and water. The organic layer was dried over magnesium sulfate, and the residue was vacuum dried, to give 35.6 g of ethyl 2-chloroisonicotinate as shown in Table 132 below.

Workup

  1. additionwas added
  2. temperaturecooling for an hour
  3. stirringthe mixture was stirred at room temperature for 2 hours
  4. concentrationThe solution was concentrated
  5. extractionextracted
  6. additionby adding ethyl acetate and water
  7. dry with materialThe organic layer was dried over magnesium sulfate
  8. customdried

Sources & evidence

ORD record
ord-cdf1400b77b34e4c9295075cd0f17d11
Source dataset
uspto-grants-2009_11
Patent number
US07619092B2

Reaction notes

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