Ethanol → 3-(3-Ethoxy-4-nitrophenyloxy)-5-methylpyrazole

HRID 644843Notes

Reaction equation

HRID 644843 reaction equation
C(=O)([O-])O.[K+].F[C:7]1[CH:8]=[C:9]([O:16][C:17]2[CH:21]=[C:20]([CH3:22])[NH:19][N:18]=2)[CH:10]=[CH:11][C:12]=1[N+:13]([O-:15])=[O:14].O.[CH2:24]([OH:26])[CH3:25]>>[CH2:24]([O:26][C:7]1[CH:8]=[C:9]([O:16][C:17]2[CH:21]=[C:20]([CH3:22])[NH:19][N:18]=2)[CH:10]=[CH:11][C:12]=1[N+:13]([O-:15])=[O:14])[CH3:25]

Participants

5

Reactant 4

HCID 702EthanolHCID 962WaterHCID 516893Potassium BicarbonateHCID 178624103-(3-Fluoro-4-nitrophenyloxy)-5-methylpyrazole

Product 1

HCID 178624163-(3-Ethoxy-4-nitrophenyloxy)-5-methylpyrazoleYield 42.3%

Procedure

Potassium hydrogencarbonate (0.15 g, 1.5 mmol) was added to a solution of 3-(3-fluoro-4-nitrophenyloxy)-5-methylpyrazole (0.36 g, 1.5 mmol) in ethanol (5 ml), and the mixture was refluxed under heating for 10 hours. After completion of the reaction, the reaction mixture was poured into water (10 ml) and extracted with ethyl acetate (10 ml×2), dried over anhydrous magnesium sulfate and filtered to remove magnesium sulfate, and the solvent was distilled off from the filtrate under reduced pressure. The resultant crude product was purified with a silica gel column (ethyl acetate/hexane=1/5), to give a yellow solid of 3-(3-ethoxy-4-nitrophenyloxy)-5-methylpyrazole (0.17 g, yield: 42.3%). mp: 123-124° C.; 1H-NMR (CDCl3, TMS, ppm): δ 1.47 (t, J=7.0 Hz, 3H), 2.33 (d, J=0.5 Hz, 3H), 4.13 (q, J=7.0 Hz, 2H), 5.73 (d, J=0.5 Hz, 1H), 6.68 (dd, J=2.5 and 9.1 Hz, 1H), 6.81 (d, J=2.5 Hz, 1H), 7.91 (d, J=9.1 Hz, 1H), 9.53 (br s, 1H).

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureunder heating for 10 hours
  3. customAfter completion of the reaction
  4. extractionextracted with ethyl acetate (10 ml×2)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customto remove magnesium sulfate
  8. distillationthe solvent was distilled off from the filtrate under reduced pressure
  9. customThe resultant crude product was purified with a silica gel column (ethyl acetate/hexane=1/5)

Sources & evidence

ORD record
ord-8fb5ce99519b47e08f75a30fc3e5bac1
Source dataset
uspto-grants-2010_04
Patent number
US07700786B2

Reaction notes

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