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

HRID 76126Notes

Reaction equation

HRID 76126 reaction equation
[Na].Cl[C:3]1[CH:8]=[C:7]([I:9])[CH:6]=[CH:5][N:4]=1.[CH2:10]([OH:13])[CH2:11][CH3:12]>>[I:9][C:7]1[CH:6]=[CH:5][N:4]=[C:3]([O:13][CH2:10][CH2:11][CH3:12])[CH:8]=1

Participants

4

Reactant 3

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

Product 1

HCID 666144104-Iodo-2-propoxy-pyridine

Procedure

0.58 g (25.06 mmol) sodium are carefully added to 40 mL n-propanol by several portions. The mixture is stirred until the metal is dissolved completely (ca. 45 min). Then 6.00 g (25.1 mmol) 2-chloro-4-iodo-pyridine are slowly added to the mixture. The mixture is stirred at reflux for 3 h. The reaction is quenched by the addition of some water. The solvent is removed in vacuo and to the residue are added 20 mL DMF/MeOH. The mixture is filtrated and the filtrate is purified by HPLC (MeOH/H2O/NH3).

Workup

  1. dissolutionis dissolved completely (ca. 45 min)
  2. stirringThe mixture is stirred
  3. temperatureat reflux for 3 h
  4. customThe reaction is quenched by the addition of some water
  5. customThe solvent is removed in vacuo and to the residue
  6. additionare added 20 mL DMF/MeOH
  7. filtrationThe mixture is filtrated
  8. customthe filtrate is purified by HPLC (MeOH/H2O/NH3)

Sources & evidence

ORD record
ord-f1cbf8f942af439f9baebddecc930ca1
Source dataset
uspto-grants-2014_09
Patent number
US08835472B2

Reaction notes

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