Water → N-[2-(1-Oxobutyl)phenyl]acetamide

HRID 476953Notes

Reaction equation

HRID 476953 reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[CH2:11][CH2:12][CH3:13])=[CH:8][CH:7]=[CH:6][CH:5]=2.I([O-])(=O)(=O)=[O:15].[Na+].[OH2:20]>CO>[O:20]=[C:10]([C:9]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:3][C:2](=[O:15])[CH3:1])[CH2:11][CH2:12][CH3:13]

Participants

5

Reactant 3

HCID 962Water2×HCID 2948532-methyl-3-propyl-1H-indoleHCID 23667635Sodium periodate

Product 1

HCID 3532789N-[2-(1-Oxobutyl)phenyl]acetamideYield 85%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2-methyl-3-propylindole (159 g) in methanol (1370 ml) was stirred under nitrogen while a solution of sodium periodate (430.4 g) in water (2450 ml) was added over a period of one hour. External cooling was applied as necessary to maintain the reaction temperature at or below 25°. After stirring at room temperature overnight, the mixture was diluted with water (7 liters) and was extracted with dichloromethane (2 liters). The phases were separated, and the aqueous layer was extracted twice more with dichloromethane (1 liter each). The combined organic phases were washed twice with water (1.5 liter each), dried (MgSO4), and evaporated to provide 246.5 grams of crude product. This material was purified by two successive chromatographies over flash silica gel, eluting the desired product with dichloromethane. Upon evaporation of the appropriate fractions, there was obtained 160.6 grams (85% yield) of the title compound as a white crystalline solid, m.p. 46.5°-47°.

Workup

  1. additionwas added over a period of one hour
  2. temperatureExternal cooling
  3. temperatureto maintain the reaction temperature at or below 25°
  4. extractionwas extracted with dichloromethane (2 liters)
  5. customThe phases were separated
  6. extractionthe aqueous layer was extracted twice more with dichloromethane (1 liter each)
  7. washThe combined organic phases were washed twice with water (1.5 liter each)
  8. dry with materialdried (MgSO4)
  9. customevaporated
  10. customto provide 246.5 grams of crude product
  11. customThis material was purified by two successive chromatographies over flash silica gel
  12. washeluting the desired product with dichloromethane
  13. customUpon evaporation of the appropriate fractions

Sources & evidence

ORD record
ord-7f8297e950d143f2a7ef9da607cba093
Source dataset
uspto-grants-1989_12
Patent number
US04886800

Reaction notes

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