N-heptyl-2-hydroxy-2-(4-hydroxy-3-methoxyphenyl)acetamide → N-heptyl-2-(4-hydroxy-3-methoxyphenyl)-2-oxoacetamide

HRID 2410614Notes

Reaction equation

HRID 2410614 reaction equation
[CH2:1]([NH:8][C:9](=[O:21])[CH:10]([OH:20])[C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[C:13]([O:18][CH3:19])[CH:12]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]>C(Cl)(Cl)Cl.[O-2].[Mn+2]>[CH2:1]([NH:8][C:9](=[O:21])[C:10]([C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[C:13]([O:18][CH3:19])[CH:12]=1)=[O:20])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

4

Reactant 1

HCID 12106248N-heptyl-2-hydroxy-2-(4-hydroxy-3-methoxyphenyl)acetamide

Product 1

HCID 49854207N-heptyl-2-(4-hydroxy-3-methoxyphenyl)-2-oxoacetamideYield 30.1%

Reagents, catalysts & solvents 2

HCID 160959Manganese oxideCatalystHCID 6212ChloroformSolvent

Procedure

Manganese oxide 60% (4.5 g, 31 mmol) was added to a stirred solution of N-heptyl-2-hydroxy-2-(4-hydroxy-3-methoxy-phenyl)-acetamide (0.5 g, 1.7 mmol) in chloroform (50 ml) at room temperature. The resulting mixture was stirred at room temperature for 24 hrs. filtered, and centrifuged to remove the remaining of manganese oxide. The filtrate was concentrated in vacuum. The crude product was chromatographed on a silica gel column using ethyl acetate/heptane (2:3) as eluent to provide the title compound (0.15 g, 30% yield) as pale yellow crystals.

Workup

  1. filtrationfiltered
  2. customto remove the
  3. concentrationThe filtrate was concentrated in vacuum
  4. customThe crude product was chromatographed on a silica gel column

Sources & evidence

ORD record
ord-6aaac9349d5d47b083282e2ec6ce979c
Source dataset
uspto-grants-2014_08
Patent number
US08816102B2

Reaction notes

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