Iodoethane → Ethyl 2,3-dichloropyridine-4-carboxylate

HRID 1508201Notes

Reaction equation

HRID 1508201 reaction equation
[Cl:1][C:2]1[C:3]([Cl:11])=[C:4]([CH:8]=[CH:9][N:10]=1)[C:5]([OH:7])=[O:6].[H-].[Na+].I[CH2:15][CH3:16]>CN(C=O)C>[CH2:15]([O:6][C:5](=[O:7])[C:4]1[CH:8]=[CH:9][N:10]=[C:2]([Cl:1])[C:3]=1[Cl:11])[CH3:16]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 27360832,3-Dichloropyridine-4-carboxylic acid

Product 1

HCID 46311339Ethyl 2,3-dichloropyridine-4-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2,3-dichloroisonicotinic acid (5.62 mmol) in 15 mL DMF were added NaH (7.31 mmol) followed by iodoethane (6.75 mmol) at 0° C. The cooling bath was removed and the mixture was stirred at RT overnight. The reaction was quenched with sat. aq. NaHCO3 solution and extracted with EtOAc. The combined organic layers were dried over MgSO4 and concentrated in vacuo. Purification by CC (KP-SIL™ from Biotage) using Hept/EtOAc (6/4) gives the desired product as yellow oil;

Workup

  1. customThe cooling bath was removed
  2. customThe reaction was quenched with sat. aq. NaHCO3 solution
  3. extractionextracted with EtOAc
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customPurification by CC (KP-SIL™ from Biotage)

Sources & evidence

ORD record
ord-ccf9cfeb327a4e019818146ffd1f8e6d
Source dataset
uspto-grants-2015_12
Patent number
US09221832B2

Reaction notes

Loading…