N-[3-fluoro-2-(hydroxyl-o-tolyl-methyl)-phenyl]-acetamide → N-[3-fluoro-2-(2-methyl-benzoyl)-phenyl]-acetamide

HRID 1294568Notes

Reaction equation

HRID 1294568 reaction equation
[F:1][C:2]1[C:3]([CH:12]([OH:20])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[CH3:19])=[C:4]([NH:8][C:9](=[O:11])[CH3:10])[CH:5]=[CH:6][CH:7]=1>C(Cl)(Cl)Cl.[O-2].[Mn+4].[O-2]>[F:1][C:2]1[C:3]([C:12](=[O:20])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[CH3:19])=[C:4]([NH:8][C:9](=[O:11])[CH3:10])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 69489997N-[3-fluoro-2-(hydroxyl-o-tolyl-methyl)-phenyl]-acetamide

Product 1

HCID 69489411N-[3-fluoro-2-(2-methyl-benzoyl)-phenyl]-acetamide

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6212ChloroformSolvent

Procedure

205 mg (0.75 mmol) N-[3-fluoro-2-(hydroxyl-o-tolyl-methyl)-phenyl]-acetamide are dissolved in 9 ml chloroform, combined with 652 mg (7.5 mmol) manganese(IV)-oxide and stirred for 3 d at ambient temperature. Then excess manganese(IV)-oxide is filtered off through Celite and the solvent is eliminated in vacuo. The crude product is purified by column chromatography. The carrier material used is silica gel and the eluant used is a mixture of cyclohexane:ethyl acetate (80:20).

Workup

  1. filtrationThen excess manganese(IV)-oxide is filtered off through Celite
  2. customThe crude product is purified by column chromatography
  3. additiona mixture of cyclohexane:ethyl acetate (80:20)

Sources & evidence

ORD record
ord-0a32ff9d21694fd790aba529c9ff32d8
Source dataset
uspto-grants-2007_07
Patent number
US07241769B2

Reaction notes

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