2-Thiophenecarboxaldehyde → 3-[(Thien-2-yl)methylene]-2-indolinone

HRID 1414865Notes

Reaction equation

HRID 1414865 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].[S:11]1[CH:15]=[CH:14][CH:13]=[C:12]1[CH:16]=O.N1CCCCC1>C1C=CC=CC=1>[S:11]1[CH:15]=[CH:14][CH:13]=[C:12]1[CH:16]=[C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[NH:1][C:2]1=[O:10]

Participants

5

Reactant 3

HCID 73642-ThiophenecarboxaldehydeHCID 8082PiperidineHCID 321710Oxindole

Product 1

HCID 3087173-[(Thien-2-yl)methylene]-2-indolinoneYield 55%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of oxindole (16.5 g, 0.12 mole), thiophene-2-carboxaldehyde (19.1 g, 0.17 mole) and piperidine (1 ml) in 200 ml of benzene is heated at reflux temperature for 4 hours, during which time water is separated by means of a Dean-Stark trap. Solvent is removed in vacuo and the residue is crystallized twice from ethanol to give 15 g of the product: m.p. 208.5°-210°.

Workup

  1. temperatureis heated
  2. temperatureat reflux temperature for 4 hours
  3. customduring which time water is separated by means of a Dean-Stark trap
  4. customSolvent is removed in vacuo
  5. customthe residue is crystallized twice from ethanol

Sources & evidence

ORD record
ord-57c90fbcee414d52977d593a51db60ca
Source dataset
uspto-grants-1977_01
Patent number
US04002749

Reaction notes

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