Salicylaldehyde → 3-(2-Hydroxybenzylidene)-6-thiophen-3-yl-1,3-dihydroindol-2-one

HRID 2120200

Reaction equation

HRID 2120200 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([C:6]2[CH:14]=[C:13]3[C:9]([CH2:10][C:11](=[O:15])[NH:12]3)=[CH:8][CH:7]=2)=[CH:2]1.[OH:16][C:17]1[CH:24]=[CH:23][CH:22]=[CH:21][C:18]=1[CH:19]=O.N1CCCCC1>C(O)C>[OH:16][C:17]1[CH:24]=[CH:23][CH:22]=[CH:21][C:18]=1[CH:19]=[C:10]1[C:9]2[C:13](=[CH:14][C:6]([C:3]3[CH:4]=[CH:5][S:1][CH:2]=3)=[CH:7][CH:8]=2)[NH:12][C:11]1=[O:15]

Participants

5

Reactant 3

HCID 6998SalicylaldehydeHCID 8082PiperidineHCID 234390276-Thiophen-3-yl-1,3-dihydroindol-2-one

Product 1

HCID 536743653-(2-Hydroxybenzylidene)-6-thiophen-3-yl-1,3-dihydroindol-2-oneYield 69%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 6-thiophen-3-yl-1,3-dihydroindol-2-one (100 mg, 0.5 mmol), 2-hyroxy-benzaldehyde (60 mg, 0.5 mmol) and piperidine (0.23 mL) in ethanol (4 mL) was stirred at reflux overnight. The precipitate was collected by vacuum filtration, washed with ethanol and dried to give 110 mg (69%) of 3-(2-hydroxybenzylidene)-6-thiophen-3-yl-1,3-dihydroindol-2-one as yellow-red crystals.

Workup

  1. temperatureat reflux overnight
  2. filtrationThe precipitate was collected by vacuum filtration
  3. washwashed with ethanol
  4. customdried

Sources & evidence

ORD record
ord-810dfb8b26d54e3086376f582cc18ff8
Source dataset
uspto-grants-2004_02
Patent number
US06689806B1

Linked notes

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