Benzoyl chloride → 1-Ethyl-5-benzoyloxindole

HRID 236364

Reaction equation

HRID 236364 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[Al+3].[Cl-].[Cl-].[N+](C1C=CC=CC=1)([O-])=O.[CH2:23]([N:25]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH2:27][C:26]1=[O:34])[CH3:24]>>[CH2:23]([N:25]1[C:33]2[C:28](=[CH:29][C:30]([C:1](=[O:8])[C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[CH:31][CH:32]=2)[CH2:27][C:26]1=[O:34])[CH3:24]

Participants

5

Reactant 4

HCID 7412Benzoyl chlorideHCID 7416NitrobenzeneHCID 66135N-EthyloxindoleHCID 6451240Aluminum(III) Chloride

Product 1

HCID 137705251-Ethyl-5-benzoyloxindoleYield 42.8%

Conditions

Temperature
100 °C

Procedure

To a mixture of 26.18 g. (186 mmoles) of benzoyl chloride and 32.95 g. of aluminum chloride in 30 ml. of nitrobenzene was gradually added 10.0 g. (62.1 mmoles) of 1-ethyloxindole. The reaction mixture was heated to 100° C. for one hour, cooled and added to 2 l. of ice-water with stirring. The mixture was extracted with methylene chloride (5×200 ml.) and the extracts dried over magnesium sulfate and concentrated in vacuo. The nitrobenzene was distilled from the residue under high vacuum and the residue treated with diethyl ether to induce crystallization. The resulting solids were filtered and recrystallized from methylene chloride petroleum ether, 7.05 g. (42.8% yield), m.p. 134°-136° C.

Workup

  1. additionTo a mixture of 26.18 g
  2. temperaturecooled
  3. additionadded to 2 l
  4. extractionThe mixture was extracted with methylene chloride (5×200 ml.)
  5. dry with materialthe extracts dried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. distillationThe nitrobenzene was distilled from the residue under high vacuum
  8. additionthe residue treated with diethyl ether
  9. customcrystallization
  10. filtrationThe resulting solids were filtered
  11. customrecrystallized from methylene chloride petroleum ether, 7.05 g

Sources & evidence

ORD record
ord-a5ad2194f2064de188c0df6f18533e41
Source dataset
uspto-grants-1987_02
Patent number
US04644005

Linked notes

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