Dimethylformamide → 2-Iodo-5-propoxypyridine

HRID 1858016Notes

Reaction equation

HRID 1858016 reaction equation
I[CH2:2][CH2:3][CH3:4].[I:5][C:6]1[N:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1.C(=O)(O)[O-].[K+].CN(C=O)C>C(Cl)Cl.O>[I:5][C:6]1[CH:7]=[CH:8][C:9]([O:12][CH2:2][CH2:3][CH3:4])=[CH:10][N:11]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 336431-IodopropaneHCID 516893Potassium BicarbonateHCID 110639836-iodopyridin-3-ol

Product 1

HCID 221255242-Iodo-5-propoxypyridine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

Iodopropane (0.18 mL, 1.8 mmol) was added dropwise to a mixture comprising 6-iodopyridin-3-ol (0.32 g, 1.14 mmol), potassium bicarbonate (0.23 g, 1.7 mmol) and DMF (2 mL). The mixture was heated at 80° C. for 1 hour, cooled and diluted with methylene chloride and water. The aqueous layer was separated and extracted with methylene chloride (20 mL). The combined organic layers were washed with water 30 mL, dried (MgSO4) and concentrated under reduced pressure to provide 2-iodo-5-propoxypyridine. MS (ESI); Calculated for C8H10NIO, 266.1, Found (MH+): 222.

Workup

  1. temperaturecooled
  2. customThe aqueous layer was separated
  3. extractionextracted with methylene chloride (20 mL)
  4. washThe combined organic layers were washed with water 30 mL
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-83809f9e206d4f349bf62a97ce46f2c2
Source dataset
uspto-grants-2000_11
Patent number
US06150379

Reaction notes

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