4-Chloro-2-methylphenol → HCID 2800136, compound

HRID 2271287Notes

Reaction equation

HRID 2271287 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([CH3:9])[CH:3]=1.[H-].[Na+].Cl[C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][N:14]=1>O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][N:14]=2)=[C:4]([CH3:9])[CH:3]=1

Participants

5

Reactant 3

HCID 148554-Chloro-2-methylphenolHCID 24758Sodium hydrideHCID 783082-Chloro-5-nitropyridine

Product 1

HCID 2800136HCID 2800136, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
22 °C

Procedure

4-Chloro-2-methylphenol (101 mg, 0.71 mmol) was dissolved in tetrahydrofuran (2.1 mL) and the solution was treated with sodium hydride (60% dispersed in mineral oil, 31 mg, 0.78 mmol). After stirring for 30 minutes at 22° C., 2-chloro-5-nitropyridine (101 mg, 0.64 mmol) was added and the reaction mixture was heated to reflux for 1 hour. The solution was cooled to ambient temperature, quenched with saturation aqueous NH4Cl and concentrated in vacuo. The residue was redissolved in ethyl acetate then washed 2× with saturated NaHCO3, saturated NaCl, dried over anhydrous Na2SO4 and concentrated in vacuo.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 1 hour
  3. temperatureThe solution was cooled to ambient temperature
  4. customquenched with saturation aqueous NH4Cl
  5. concentrationconcentrated in vacuo
  6. dissolutionThe residue was redissolved in ethyl acetate
  7. washthen washed 2× with saturated NaHCO3, saturated NaCl
  8. dry with materialdried over anhydrous Na2SO4
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3d4bf74a49e343bbb82a54235dde2d41
Source dataset
uspto-grants-2001_12
Patent number
US06333341B1

Reaction notes

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