Acetaldehyde → 3-ethylidene-1H-indol-2-one

HRID 74532Notes

Reaction equation

HRID 74532 reaction equation
[CH:1](=O)[CH3:2].[NH:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][C:5]1=[O:13].N1CCCCC1>CO>[CH:1](=[C:6]1[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[NH:4][C:5]1=[O:13])[CH3:2]

Participants

5

Reactant 3

HCID 177AcetaldehydeHCID 8082PiperidineHCID 321710Oxindole

Product 1

HCID 534256623-ethylidene-1H-indol-2-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.85 mL (15 mmol) acetaldehyde were added dropwise to 2.0 g (15 mmol) indolin-2-one and 0.20 mL piperidine in 20 mL methanol. The reaction mixture was refluxed for 3 h and then evaporated down. The residue was triturated in diisopropylether and suction filtered.

Workup

  1. temperatureThe reaction mixture was refluxed for 3 h
  2. customevaporated down
  3. customThe residue was triturated in diisopropylether
  4. filtrationsuction filtered

Sources & evidence

ORD record
ord-4f5a8908f17643f28c7d53c5f12ff7b8
Source dataset
uspto-grants-2014_09
Patent number
US08829006B2

Reaction notes

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