2,4-Dihydroxybenzaldehyde → 3-[(2,4-Dihydroxyphenyl)methylidene]-1,3-dihydro-2H-indol-2-one

HRID 2190102Notes

Reaction equation

HRID 2190102 reaction equation
[N:1]1[C:2](=[O:10])[CH:3]=[C:4]2[C:9]=1[CH:8]=[CH:7][CH:6]=[CH:5]2.[OH:11][C:12]1[CH:19]=[C:18]([OH:20])[CH:17]=[CH:16][C:13]=1[CH:14]=O>N1CCCCC1.C(O)C>[OH:11][C:12]1[CH:19]=[C:18]([OH:20])[CH:17]=[CH:16][C:13]=1[CH:14]=[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 2

HCID 72132,4-DihydroxybenzaldehydeHCID 17904787Indol-2-one

Product 1

HCID 686168283-[(2,4-Dihydroxyphenyl)methylidene]-1,3-dihydro-2H-indol-2-one

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 702EthanolSolvent

Procedure

A mixture of 1.33 g of indole-2-one (10 mmol), 1.38 g of 2,4-dihydroxybenzaldehyde (10 mmol) and 3 drops of piperidine are refluxed in 40 ml of ethanol for 5 hours. The desired product precipitates as a yellow solid during the reaction. After cooling to room temperature, the product is filtered off, washed with ethanol and dried in vacuo. Yield 1.28 g (51%).

Workup

  1. customThe desired product precipitates as a yellow solid during the reaction
  2. filtrationthe product is filtered off
  3. washwashed with ethanol
  4. customdried in vacuo

Sources & evidence

ORD record
ord-4fc6df65fb564f64aa648f8ec1e5e8c5
Source dataset
uspto-grants-2012_12
Patent number
US08324267B2

Reaction notes

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