Sodium ethoxide → 7-Chloro-1,3-dihydro-2H-indol-2-one

HRID 971429Notes

Reaction equation

HRID 971429 reaction equation
[O-]CC.[Na+].[Na].[Cl:6][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:15]=1[NH:14][C:13](=[O:16])[C:12]2=NN>C(O)C>[Cl:6][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:15]=1[NH:14][C:13](=[O:16])[CH2:12]2

Participants

5

Reactant 3

HCID 2723922Sodium ethoxideHCID 5360545SodiumHCID 178514328HCID 178514328, compound

Product 1

HCID 37310107-Chloro-1,3-dihydro-2H-indol-2-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of sodium ethoxide prepared by heating 5.5 g. of sodium in 200 ml. of ethanol at 70° C. is added 17 g. of 7-chloro-3-hydrazono-oxindole over a period of 3.5 hours, and the resulting solution is heated at 70° C. for 24 hours. The solvent is evaporated in vacuo, the residue dissolved in water, acidified with 6 N. hydrochloric acid and the resulting precipitate recovered by filtering, washed three times with water, dried by suction and crystallized from methylene chloride/ether to obtain 7-chlorooxindole, 218°-220° C.

Workup

  1. temperatureby heating 5.5 g
  2. customThe solvent is evaporated in vacuo
  3. dissolutionthe residue dissolved in water
  4. customhydrochloric acid and the resulting precipitate recovered
  5. filtrationby filtering
  6. washwashed three times with water
  7. customdried by suction
  8. customcrystallized from methylene chloride/ether

Sources & evidence

ORD record
ord-8b677553246644d2bcd419385f9b4f85
Source dataset
uspto-grants-1979_07
Patent number
US04160032

Reaction notes

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