Sodium hydride → 2-(4-Chloropyridin-2-yloxy)-4,5-dichlorobenzenamine

HRID 588789Notes

Reaction equation

HRID 588789 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([Cl:9])=[CH:4][C:3]=1[OH:10].[H-].[Na+].[Cl:13][C:14]1[CH:19]=[CH:18][N:17]=[C:16](F)[CH:15]=1>C1COCC1>[Cl:13][C:14]1[CH:19]=[CH:18][N:17]=[C:16]([O:10][C:3]2[CH:4]=[C:5]([Cl:9])[C:6]([Cl:8])=[CH:7][C:2]=2[NH2:1])[CH:15]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 27628394-Chloro-2-fluoropyridineHCID 30154152-Amino-4,5-dichlorophenol

Product 1

HCID 1176071602-(4-Chloropyridin-2-yloxy)-4,5-dichlorobenzenamineYield 45%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-amino-4,5-dichlorophenol (1.5 g, 8.47 mmol) in THF (20 mL) at 0° C., NaH (60% dispersed in oil, 373 mg, 9.33 mmol) was added and the resulting mixture was stirred for 20 min. To this mixture, 4-chloro-2-fluoropyridine (1.67 g, 12.7 mmol) was added and the resulting mixture was stirred at reflux under argon for 15 h. The mixture was allowed to cool to room temperature and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (petroleum ether/ethyl acetate=20:1 to 10:1) to afford the desired product (1.1 g, 45% yield). ESI-MS m/z: 287.0 [M−H]−.

Workup

  1. stirringthe resulting mixture was stirred
  2. temperatureat reflux under argon for 15 h
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by flash column chromatography on silica gel (petroleum ether/ethyl acetate=20:1 to 10:1)

Sources & evidence

ORD record
ord-72729ac48648442da4a5385bfc265a6b
Source dataset
uspto-grants-2016_01
Patent number
US09227978B2

Reaction notes

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