Water → 2-(Pyridin-2-ylmethoxy)-5-nitropyridine

HRID 427721Notes

Reaction equation

HRID 427721 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][OH:8].[H-].[Na+].Cl[C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][N:13]=1.O>CN(C)C=O>[N+:18]([C:15]1[CH:16]=[CH:17][C:12]([O:8][CH2:7][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)=[N:13][CH:14]=1)([O-:20])=[O:19]

Participants

6

Reactant 4

HCID 962WaterHCID 11474PiconolHCID 24758Sodium hydrideHCID 783082-Chloro-5-nitropyridine

Product 1

HCID 183577252-(Pyridin-2-ylmethoxy)-5-nitropyridineYield 91%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
-20 °C

Procedure

2-Pyridylcarbinol (7.5 g, 0.069 mole) in dry dimethylformamide (190 ml) was cooled to −20° C. and treated with an 80% dispersion of sodium hydride in mineral oil (2.07 g, 0.069 mole) under argon. The mixture was stirred at −20° C. for two hours. 2-Chloro-5-nitropyridine (8.83 g, 0.058 mole) was added and the mixture was stirred at −20° C. for 0.5 hour then warmed to room temperature and stirred for 18 hours. Water was added dropwise and the solvent removed in vacuo. The residue was dissolved in dichloromethane, washed with 10% aqueous sodium hydroxide solution followed by water, dried (Na2SO4) and evaporated in vacuo to afford the title compound (12.2 g, 91%) as an orange solid.

Workup

  1. stirringthe mixture was stirred at −20° C. for 0.5 hour
  2. temperaturethen warmed to room temperature
  3. stirringstirred for 18 hours
  4. customthe solvent removed in vacuo
  5. dissolutionThe residue was dissolved in dichloromethane
  6. washwashed with 10% aqueous sodium hydroxide solution
  7. dry with materialdried (Na2SO4)
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-38584da362c34bb981648c892a606595
Source dataset
uspto-grants-2001_11
Patent number
US06313145B1

Reaction notes

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