Water → 2-Methyl-3-((5-nitropyridin-2-yl)oxy)pyridine

HRID 840547Notes

Reaction equation

HRID 840547 reaction equation
[OH:1][C:2]1[C:3]([CH3:8])=[N:4][CH:5]=[CH:6][CH:7]=1.[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=O)C>[CH3:8][C:3]1[C:2]([O:1][C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][N:13]=2)=[CH:7][CH:6]=[CH:5][N:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 707192-Methylpyridin-3-olHCID 783082-Chloro-5-nitropyridine

Product 1

HCID 106095382-Methyl-3-((5-nitropyridin-2-yl)oxy)pyridineYield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

3-Hydroxy-2-methylpyridine (40 g, 0.37 mole) in dry DMF (1.3 L) under argon was cooled to 0° C. Sodium hydride (11.1 g of an 80% dispersion in oil, 0.37 mole) was added portionwise and the mixture stirred at 0° C. for 15 minutes and then room temperature for 3 hours. 2-Chloro-5-nitropyridine (58.6 g, 0.37 mole) was added and the mixture stirred for 18 hours at r.t. Water (50 ml) was added dropwise and the solvent was removed in vacuo. The residue was dissolved in CH2Cl2, washed with 10% aqueous sodium hydroxide, and water, dried (Na2SO4) and evaporated in vacuo to afford the title compound (81.1 g, 95%) as a yellow solid.

Workup

  1. waitroom temperature for 3 hours
  2. stirringthe mixture stirred for 18 hours at r.t
  3. customthe solvent was removed in vacuo
  4. dissolutionThe residue was dissolved in CH2Cl2
  5. washwashed with 10% aqueous sodium hydroxide, and water
  6. dry with materialdried (Na2SO4)
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-fbff1a71205a403da5b87a4f9bd0465c
Source dataset
uspto-grants-2002_04
Patent number
US06369060B1

Reaction notes

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