4-Chloro-2-methylphenol → 2-(4-Chloro-2-methyl-phenoxy)-3-methyl-5-nitropyridine

HRID 635003Notes

Reaction equation

HRID 635003 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[C:6]([CH3:11])[CH:5]=1.Cl[C:13]1[C:18]([CH3:19])=[CH:17][C:16]([N+:20]([O-:22])=[O:21])=[CH:15][N:14]=1>O1CCCC1>[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][C:13]2[C:18]([CH3:19])=[CH:17][C:16]([N+:20]([O-:22])=[O:21])=[CH:15][N:14]=2)=[C:6]([CH3:11])[CH:5]=1

Participants

5

Reactant 3

HCID 148554-Chloro-2-methylphenolHCID 24758Sodium hydrideHCID 896482-Chloro-3-methyl-5-nitropyridine

Product 1

HCID 184194612-(4-Chloro-2-methyl-phenoxy)-3-methyl-5-nitropyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (60% in mineral oil, 1.08 g, 27 mmol) was washed 3× with hexanes then a solution of 4-chloro-2-methylphenol (3.50 g, 24.5 mmol) dissolved in tetrahydrofuran (40 mL) was added. The solution was stirred for 20 minutes then 2-chloro-3-methyl-5-nitropyridine (4.02 g, 23.3 mmol) was added and the reaction mixture was heated to reflux for 3 hours. After cooling, the mixture was concentrated in vacuo then dissolved in ethyl acetate and washed with water, 3× with saturated NaHCO3− and saturated NaCl then dried over Na2SO4 and concentrated in vacuo.

Workup

  1. additionwas added
  2. temperaturethe reaction mixture was heated
  3. temperatureto reflux for 3 hours
  4. temperatureAfter cooling
  5. concentrationthe mixture was concentrated in vacuo
  6. dissolutionthen dissolved in ethyl acetate
  7. washwashed with water, 3× with saturated NaHCO3− and saturated NaCl
  8. dry with materialthen dried over Na2SO4
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-daa795dac1e240708b9450abc8c84188
Source dataset
uspto-grants-2001_02
Patent number
US06184237B2

Reaction notes

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