2-Chlorophenol → 3-(2-Chlorophenoxy)-4-nitro-1-oxo-1lambda~5~-pyridine

HRID 1448142Notes

Reaction equation

HRID 1448142 reaction equation
F[C:2]1[CH:3]=[N+:4]([O-:11])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].[Cl:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[OH:19].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[O:19][C:2]1[CH:3]=[N+:4]([O-:11])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 72452-ChlorophenolHCID 11430Potassium CarbonateHCID 5940283-Fluoro-4-nitropyridin-1-ium-1-olate

Product 1

HCID 112309183-(2-Chlorophenoxy)-4-nitro-1-oxo-1lambda~5~-pyridine

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 3.16 g of 3-fluoro-4-nitropyridine N-oxide [Rocz. Chem. 40, 1675 (1966), Chem. Abstr. 69, 59059d (1968)] and 2.58 g of o-chlorophenol in 250 ml of acetone is treated with 5.6 g of anhydrous potassium carbonate. The heterogeneous mixture is stirred vigorously at 25° C. for 16 hours. The mixture is filtered and concentrated at reduced pressure. The product is dissolved in 200 ml of acetonitrile and chromatographed over neutral alumina. The eluate is concentrated at reduced pressure and 3-(o-chlorophenoxy)-4-nitropyridine N-oxide is recrystallized from methanol-diethyl ether; mp 129°-131° C.

Workup

  1. filtrationThe mixture is filtered
  2. concentrationconcentrated at reduced pressure
  3. dissolutionThe product is dissolved in 200 ml of acetonitrile
  4. customchromatographed over neutral alumina
  5. concentrationThe eluate is concentrated at reduced pressure and 3-(o-chlorophenoxy)-4-nitropyridine N-oxide
  6. customis recrystallized from methanol-diethyl ether

Sources & evidence

ORD record
ord-788d2e30d0b44fb5920716b84257d5bc
Source dataset
uspto-grants-1979_12
Patent number
US04179563

Reaction notes

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