Acetyl chloride → 1-Ethyl-5-acetyloxindole

HRID 1788966Notes

Reaction equation

HRID 1788966 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[Cl-].[Al+3].[Cl-].[Cl-].[N+](C1C=CC=CC=1)([O-])=O.[CH2:18]([N:20]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH2:22][C:21]1=[O:29])[CH3:19]>>[CH2:18]([N:20]1[C:28]2[C:23](=[CH:24][C:25]([C:1](=[O:3])[CH3:2])=[CH:26][CH:27]=2)[CH2:22][C:21]1=[O:29])[CH3:19]

Participants

5

Reactant 4

HCID 6367Acetyl chlorideHCID 7416NitrobenzeneHCID 66135N-EthyloxindoleHCID 6451240Aluminum(III) Chloride

Product 1

HCID 137705311-Ethyl-5-acetyloxindoleYield 57.3%

Conditions

Temperature
45 °C

Procedure

To a mixture of 29.25 g. (0.373 mole) of acetyl chloride and 65.9 g. of aluminum chloride in 60 ml. of nitrobenzene was added gradually 20.0 (0.124 mole) of 1-ethyloxindole. The reaction warmed to about 45° C. with an evolution of gas. After stirring for one hour the reaction was heated to 100° C. for one hour and allowed to stir at room temperature over night. The reaction mixture was poured into 2 l. of ice with stirring. After 30 minutes the product was filtered, air dried and dissolved in 200 ml. of methylene chloride. The solution was dried over magnesium sulfate and concentrated to dryness. The residue was recrystallized from toluene, 14.44 g. (57.3% yield), m.p. 141°-45° C.

Workup

  1. additionTo a mixture of 29.25 g
  2. temperaturewas heated to 100° C. for one hour
  3. stirringto stir at room temperature over night
  4. additionThe reaction mixture was poured into 2 l
  5. stirringof ice with stirring
  6. filtrationAfter 30 minutes the product was filtered
  7. customair dried
  8. dissolutiondissolved in 200 ml
  9. dry with materialThe solution was dried over magnesium sulfate
  10. concentrationconcentrated to dryness
  11. customThe residue was recrystallized from toluene, 14.44 g

Sources & evidence

ORD record
ord-48aae4233540416d98923fe7e4089d35
Source dataset
uspto-grants-1987_08
Patent number
US04686224

Reaction notes

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