Sulfuric Acid → HCID 56994825, compound

HRID 845493Notes

Reaction equation

HRID 845493 reaction equation
CCCC[C:5](=[O:15])[C:6]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:7].S(=O)(=O)(O)O>>[CH2:14]([CH:12]1[CH2:11][CH2:10][CH:9]2[CH:14]([C:5](=[O:15])[C:6](=[O:7])[NH:8]2)[CH2:13]1)[CH2:9][CH2:10][CH3:11]

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 179609Hexanamide, 2-oxo-N-phenyl-

Product 1

HCID 56994825HCID 56994825, compound

Procedure

For example, a solution of 4-n-butylglyoxylanilide (II), (12.2 g, 0.01 mole) is added to concentrated sulfuric acid (23 ml) at 50° C. while maintaining the reaction mixture by cooling below 65° C. The mixture is held at 65° C. for one hour an poured unto ice with stirring. A reddish-orange precipitate is formed and is washed with water. Recrystallization from ethanol yields pure 5-n-butyl-octahydro-2,3-dioxo-1H-indole (III) with mp 112°-113° C.

Workup

  1. temperaturewhile maintaining the reaction mixture
  2. temperatureby cooling below 65° C
  3. additionan poured unto ice
  4. customA reddish-orange precipitate is formed
  5. washis washed with water
  6. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-961018c4a0524665838f101cf30c3938
Source dataset
uspto-grants-1988_07
Patent number
US04758585

Reaction notes

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