1-Propanol → 4-Iodo-2-propoxy-pyridine

HRID 330816Notes

Reaction equation

HRID 330816 reaction equation
[Na].[CH2:2]([OH:5])[CH2:3][CH3:4].Cl[C:7]1[CH:12]=[C:11]([I:13])[CH:10]=[CH:9][N:8]=1>O>[I:13][C:11]1[CH:10]=[CH:9][N:8]=[C:7]([O:5][CH2:2][CH2:3][CH3:4])[CH:12]=1

Participants

5

Reactant 3

HCID 10311-PropanolHCID 15165112-Chloro-4-iodopyridineHCID 5360545Sodium

Product 1

HCID 666144104-Iodo-2-propoxy-pyridine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

0.58 g (25 mmol) sodium are carefully added to 40 mL n-propanol in several portions. The mixture is stirred for 45 min. After that time, 6.0 g (25 mmol) 2-chloro-4-iodo-pyridine are slowly added to the mixture. The mixture is stirred at reflux for 3 h. Subsequently, water is added and the solvent is removed in vacuo. The residue is taken up in 20 mL DMF/MeOH, filtrated and the filtrate is purified by RP-HPLC (MeOH/H2O/NH3).

Workup

  1. stirringThe mixture is stirred
  2. temperatureat reflux for 3 h
  3. customthe solvent is removed in vacuo
  4. filtrationfiltrated
  5. customthe filtrate is purified by RP-HPLC (MeOH/H2O/NH3)

Sources & evidence

ORD record
ord-f3c3eb2351a14199ab662644accaefa1
Source dataset
uspto-grants-2014_11
Patent number
US08877754B2

Reaction notes

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