1-Propanol → 2-Bromo-4-propoxypyridine

HRID 225762Notes

Reaction equation

HRID 225762 reaction equation
[Na].[Br:2][C:3]1[CH:8]=[C:7]([N+]([O-])=O)[CH:6]=[CH:5][N:4]=1.[CH2:12]([OH:15])[CH2:13][CH3:14]>>[Br:2][C:3]1[CH:8]=[C:7]([O:15][CH2:12][CH2:13][CH3:14])[CH:6]=[CH:5][N:4]=1

Participants

4

Reactant 3

HCID 10311-PropanolHCID 2430152-Bromo-4-nitropyridineHCID 5360545Sodium

Product 1

HCID 230921272-Bromo-4-propoxypyridineYield 58%

Conditions

Temperature
95 °C

Procedure

To a solution of sodium (480 mg, 21 mmol) dissolved in 1-propanol (45 mL), was added 2-bromo-4-nitropyridine [(3.2 g, 19.2 mmol), J. Med. Chem. 46(7), 1273-1276; 2003] and the mixture was heated at 95° C. for 2 hours. The solvent was then evaporated under reduced pressure and the residue was suspended in chloroform and filtered. The filtrate was washed with water, dried over magnesium sulfate, and concentrated in vacuo to give an oily residue. The residue was distilled and title product was obtained during a temperature range of 145-150° C., as a solid in 58% yield, 2.67 g.

Workup

  1. customThe solvent was then evaporated under reduced pressure
  2. filtrationfiltered
  3. washThe filtrate was washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customto give an oily residue
  7. distillationThe residue was distilled

Sources & evidence

ORD record
ord-a5655937229e4987b651a83b6107d8aa
Source dataset
uspto-grants-2009_07
Patent number
US07557121B2

Reaction notes

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