Potassium Permanganate → methyl 2-[2-[(E)-N-methoxy-C-[3-(trifluoromethyl)phenyl]carbonimidoyl]phenyl]-2-oxoacetate

HRID 2226120Notes

Reaction equation

HRID 2226120 reaction equation
CO/C=[C:4](\[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1/[C:15](/[C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[CH:20]=1)=[N:16]/[O:17][CH3:18])/[C:5]([O:7][CH3:8])=[O:6].[Mn]([O-])(=O)(=O)=[O:30].[K+].S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+]>ClCCl.O.S([O-])(O)(=O)=O.C([N+](CCCCCC)(CCCCCC)CCCCCC)CCCCC>[CH3:18][O:17]/[N:16]=[C:15](\[C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:27])([F:26])[F:28])[CH:20]=1)/[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[C:4](=[O:30])[C:5]([O:7][CH3:8])=[O:6]

Participants

7

Reactant 3

HCID 516875Potassium PermanganateHCID 656671Sodium PyrosulfiteHCID 137550390methyl (E)-3-methoxy-2-[2-[(E)-N-methoxy-C-[3-(trifluoromethyl)phenyl]carbonimidoyl]phenyl]prop-2-enoate

Product 1

HCID 140367388methyl 2-[2-[(E)-N-methoxy-C-[3-(trifluoromethyl)phenyl]carbonimidoyl]phenyl]-2-oxoacetateYield 54.4%

Reagents, catalysts & solvents 3

HCID 110158481-Hexanaminium, N,N,N-trihexyl-, sulfate (1:1)CatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of (E,E)-methyl 3-methoxy-2-[2-(methyl(3-trifluoromethyl-phenyl)oximinomethyl)phenyl]propenoate (2.0 g as prepared in EP-A-0370629) in dichloromethane (20 ml) was added to potassium permanganate (0.93g) in water (20 ml) containing tetra-n-hexyl-ammonium hydrogensulphate (0.1 g). After stirring for 2 hours, the reaction mixture was poured into sodium metabisulphite solution (40 mls of a 10% aqueous solution) and extracted with dichloromethane. The combined organic extracts were dried, concentrated and chromatographed using a mixture of ether and hexane (1:1) as the eluant to give (E)-methyl 2-[methyl(3-trifluoromethylphenyl)oximinomethyl]phenylglyoxalate (1.01 g, 54% yield) as a clear oil; 1H NMR : δ2.31(3H,s), 3.92(3H,s), 5.60(2H,s), 7.4-7.9(8H,m) ppm; IR maxima (film): 1740, 1686 cm-1.

Workup

  1. extractionextracted with dichloromethane
  2. customThe combined organic extracts were dried
  3. concentrationconcentrated
  4. customchromatographed
  5. additiona mixture of ether and hexane (1:1) as the eluant

Sources & evidence

ORD record
ord-63696556df714fc190041182ca528e2d
Source dataset
uspto-grants-1994_09
Patent number
US05346902

Reaction notes

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