Sodium → 4-Chloro-1,3-dihydro-2H-indol-2-one

HRID 1906570Notes

Reaction equation

HRID 1906570 reaction equation
[Na].[Cl:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[C:5](=NN)[C:6](=[O:12])[NH:7]2>C(O)C>[Cl:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH2:5][C:6](=[O:12])[NH:7]2

Participants

4

Reactant 2

HCID 5360545SodiumHCID 178514322HCID 178514322, compound

Product 1

HCID 14806864-Chloro-1,3-dihydro-2H-indol-2-oneYield 60.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 22 g of sodium in 450 ml of anhydrous ethanol was added, portionwise, 43.5 g of 4-chloro-3-hydrazono-2-oxindole, and the resulting solution was heated under reflux for 30 minutes. The cooled solution was then concentrated to a gum, which was dissolved in 400 ml of water and decolorized using activated carbon. The resulting solution was poured onto a mixture of 1 liter of water and 45 ml of concentrated hydrochloric acid. The precipitate which formed was recovered by filtration, dried and recrystallized from ethanol, giving 22.4 g of 4-chloro-2-oxindole, mp 216°-218° C. (dec).

Workup

  1. temperatureunder reflux for 30 minutes
  2. concentrationThe cooled solution was then concentrated to a gum, which
  3. dissolutionwas dissolved in 400 ml of water
  4. additionThe resulting solution was poured onto a mixture of 1 liter of water and 45 ml of concentrated hydrochloric acid
  5. customThe precipitate which formed
  6. filtrationwas recovered by filtration
  7. customdried
  8. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-ac4aebe4a8a6474bb53b534329589c0f
Source dataset
uspto-grants-1987_03
Patent number
US04652658

Reaction notes

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