4-Ethyl-2-hydroxy-5-nitrohexanamide → HCID 14329816, compound

HRID 868228Notes

Reaction equation

HRID 868228 reaction equation
[CH2:1]([CH:3]([CH:10]([N+:12]([O-:14])=[O:13])[CH3:11])[CH2:4][CH:5]([OH:9])[C:6]([NH2:8])=[O:7])[CH3:2]>C(O)(=O)C.[O-2].[O-2].[O-2].[Cr+6]>[CH2:1]([CH:3]([CH:10]([N+:12]([O-:14])=[O:13])[CH3:11])[CH2:4][C:5](=[O:9])[C:6]([NH2:8])=[O:7])[CH3:2]

Participants

4

Reactant 1

HCID 198516704-Ethyl-2-hydroxy-5-nitrohexanamide

Product 1

HCID 14329816HCID 14329816, compoundYield 14%

Reagents, catalysts & solvents 2

HCID 10219390chromium (VI) trioxideCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 4-ethyl-2-hydroxy-5-nitrohexanamide (0.36 g) in acetic acid (5 ml) was added chromium trioxide (0.23 g). The resulting mixture was heated at 100° C. for 40 minutes with stirring. After cooling, the mixture was evaporated to dryness. The resulting residue was diluted with water and then extracted with ethyl acetate. The extract was washed successively with water, an aqueous sodium bicarbonate and brine, and then dried over magnesium sulfate. The solvent was removed by distillation to give an oil. The oil was purified by a preparative thin layer chromatography [solvent:methanol-chloroform (5:95)] to give 4-ethyl-5-nitro-2-oxo-hexanamide (50 mg).

Workup

  1. temperatureAfter cooling
  2. customthe mixture was evaporated to dryness
  3. additionThe resulting residue was diluted with water
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed successively with water
  6. dry with materialan aqueous sodium bicarbonate and brine, and then dried over magnesium sulfate
  7. customThe solvent was removed by distillation
  8. customto give an oil
  9. customThe oil was purified by a preparative thin layer chromatography [solvent:methanol-chloroform (5:95)]

Sources & evidence

ORD record
ord-09df9f16f9e642d7946d50fe790340d3
Source dataset
uspto-grants-1988_10
Patent number
US04778804

Reaction notes

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