Pyridine → (2,4-Difluoro-phenyl)-(3-methoxy-phenyl)-methanone oxime

HRID 852078Notes

Reaction equation

HRID 852078 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=1)=O.N1C=CC=CC=1.Cl.[NH2:26][OH:27].C(OCC)(=O)C>CCCCCCC>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=1)=[N:26][OH:27]

Participants

6

Reactant 4

HCID 1049PyridineHCID 8857Ethyl AcetateHCID 443297Hydroxyamine hydrochlorideHCID 17906337(2,4-Difluorophenyl)(3-methoxyphenyl)methanone

Product 1

HCID 72465824(2,4-Difluoro-phenyl)-(3-methoxy-phenyl)-methanone oximeYield 99%

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

Procedure

Combine (2,4-difluoro-phenyl)-(3-methoxy-phenyl)-methanone (51.2 g, 0.206 mol) and pyridine (293.4 g, 300 mL). Add hydroxylamine hydrochloride (21.7 g, 0.312 mol) and heat to 100° C., under a nitrogen atmosphere, for 4 hours. TLC (20% ethyl acetate in heptane) shows that the reaction is complete. Concentrate the reaction mixture and dry (vacuum at 50° C.). Distribute the material between ethyl acetate and water. Wash the organic layer with 10% HCl, saturated sodium chloride, dry (MgSO4) and concentrated to obtain the title compound as a white solid (53.66 g, 99% Yield). Use compound in a crude form or recrystallize from heptane and dry (P2O5). NMR and MS are consistent with the final, desired compound, which is a mixture of the Z-isomer (81%) and the E-isomer (19%). mp=122° C.-127° C.

Workup

  1. concentrationConcentrate the reaction mixture
  2. customdry (vacuum at 50° C.)
  3. washWash the organic layer with 10% HCl, saturated sodium chloride
  4. dry with materialdry (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-29c3e4da9edd4a1bba5d4c9a6b16122d
Source dataset
uspto-grants-2007_08
Patent number
US07253165B2

Reaction notes

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