Iodoethane → 2-Chloro-5-ethoxy-4-iodopyridine

HRID 1640903Notes

Reaction equation

HRID 1640903 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([OH:8])=[C:4]([I:9])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:16](I)[CH3:17]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([I:9])[C:5]([O:8][CH2:16][CH3:17])=[CH:6][N:7]=1

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 533020386-Chloro-4-iodopyridin-3-ol

Product 1

HCID 534383202-Chloro-5-ethoxy-4-iodopyridineYield 94.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

Treat a solution of 6-chloro-4-iodo-pyridin-3-ol (4.9 g, 19 mmol) and potassium carbonate (8.0 g, 58 mmol) in DMF (50 mL) with ethyl iodide (4.7 mL, 58 mmol). Heat the mixture at 60° C. for 3 h. Cool the mixture to RT and filter through filter paper. Dilute the mixture with ethyl acetate and wash with a 10% aqueous citric acid solution. Combine the aqueous solutions and extract with two additional portions of ethyl acetate. Combine the organic extracts and wash with three portions of water, one portion of saturated aqueous sodium chloride, dry over sodium sulfate, filter, and concentrate in vacuo to give the title compound 5.1 g (93%) as a brown solid. 1H NMR (400 MHz, DMSO-d6) δ 8.00 (s, 1H), 7.93 (s, 1H), 4.18 (q, J=7 Hz, 2H), 1.35 (t, J=7 Hz, 3H).

Workup

  1. temperatureCool the mixture to RT
  2. filtrationfilter
  3. filtrationthrough filter paper
  4. additionDilute the mixture with ethyl acetate
  5. washwash with a 10% aqueous citric acid solution
  6. extractionextract with two additional portions of ethyl acetate
  7. washwash with three portions of water, one portion of saturated aqueous sodium chloride
  8. dry with materialdry over sodium sulfate
  9. filtrationfilter
  10. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-7d530ea3b3e448d08c683645bcf330ac
Source dataset
uspto-grants-2012_02
Patent number
US08114872B2

Reaction notes

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