Nitrobenzene → 1-Ethyl-5-(2-thenoyl)oxindole

HRID 236374

Reaction equation

HRID 236374 reaction equation
[C:1]1([C:6](Cl)=[O:7])[S:5][CH:4]=[CH:3][CH:2]=1.[N+](C1C=CC=CC=1)([O-])=O.[Cl-].[Al+3].[Cl-].[Cl-].[CH2:22]([N:24]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH2:26][C:25]1=[O:33])[CH3:23]>O>[CH2:22]([N:24]1[C:32]2[C:27](=[CH:28][C:29]([C:6](=[O:7])[C:1]3[S:5][CH:4]=[CH:3][CH:2]=3)=[CH:30][CH:31]=2)[CH2:26][C:25]1=[O:33])[CH3:23]

Participants

6

Reactant 4

HCID 7416NitrobenzeneHCID 66135N-EthyloxindoleHCID 789282-Thiophenecarbonyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 137705281-Ethyl-5-(2-thenoyl)oxindoleYield 47.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

To a mixture of 27.3 g. (19.9 mmoles) of 2-thenoyl chloride, 30 ml. of nitrobenzene and 32.95 g. of aluminum chloride was gradually added 10 g. (62 mmoles) of 1-ethyloxindole, and the resulting reaction mixture heated at 100° C. for 75 minutes. The reaction was cooled to room temperature and poured into 2 l. of ice and water. The product was extracted with methylene chloride and the dried extract concentrated to dryness, 11.05 g. The product was recrystallized from methylene chloride-hexane, 8.03 g. (47.7% yield)m, m.p. 158°-160° C.

Workup

  1. additionTo a mixture of 27.3 g
  2. temperatureThe reaction was cooled to room temperature
  3. additionpoured into 2 l
  4. extractionThe product was extracted with methylene chloride
  5. extractionthe dried extract
  6. concentrationconcentrated to dryness, 11.05 g
  7. customThe product was recrystallized from methylene chloride-hexane, 8.03 g

Sources & evidence

ORD record
ord-5129419c816d4a35b034d0f56266c34c
Source dataset
uspto-grants-1987_02
Patent number
US04644005

Linked notes

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