Benzaldehyde → HCID 281323, compound

HRID 1414861Notes

Reaction equation

HRID 1414861 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C:2]1=[O:10].[CH:11](=O)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.N1CCCCC1>C1C=CC=CC=1>[CH:11](=[C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[NH:1][C:2]1=[O:10])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 8082PiperidineHCID 321710Oxindole

Product 1

HCID 281323HCID 281323, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of oxindole (49.5 g, 0.37 mole), benzaldehyde (50 ml, 0.5 mole) and piperidine (2 ml) in 500 ml of benzene is heated at reflux temperature, with removal of water, for one hour. Benzene is removed in vacuo and the residue is crystallized from ethanol to give 69.6 g of 3-benzylidene indolin-2-one (m.p. 177°-179°).

Workup

  1. temperatureat reflux temperature
  2. customwith removal of water
  3. customBenzene is removed in vacuo
  4. customthe residue is crystallized from ethanol

Sources & evidence

ORD record
ord-026cf5fef4334018a30cab511406a0a0
Source dataset
uspto-grants-1977_01
Patent number
US04002749

Reaction notes

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