2-Chloro-5-nitropyridine → 5-Nitro-2-phenoxypyridine

HRID 1956407Notes

Reaction equation

HRID 1956407 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.O.O.O.[O-:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[Na+]>CN(C=O)C>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([O:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[N:3][CH:4]=1)([O-:10])=[O:9]

Participants

4

Reactant 2

HCID 783082-Chloro-5-nitropyridineHCID 23681143Sodium Phenoxide Trihydrate

Product 1

HCID 32523715-Nitro-2-phenoxypyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Chloro-5-nitropyridine (4.48 g) was added in portions to a mixture of sodium phenoxide trihydrate (4.80 g) in DMF (140 ml) with stirring at ambient temperature under nitrogen. The mixture was then heated at 60° C. for 2 hours and then at 90° C. for 3 hours. The mixture was allowed to cool over 18 hours. The mixture was poured into ice water and extracted with dichloromethane to give a residue which was stirred in petroleum ether, b.p. 60°-80° C. at ambient temperature for 30 minutes and then filtered to give 5-nitro-2-phenoxypyridine, m.p. 84°-86° C.

Workup

  1. temperatureThe mixture was then heated at 60° C. for 2 hours
  2. temperatureto cool over 18 hours
  3. extractionextracted with dichloromethane
  4. customto give a residue which
  5. waitb.p. 60°-80° C. at ambient temperature for 30 minutes
  6. filtrationfiltered

Sources & evidence

ORD record
ord-eea3d8c3874e4f1499c3e68871a2fe5b
Source dataset
uspto-grants-1998_07
Patent number
US05780482

Reaction notes

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