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

HRID 2120198Notes

Reaction equation

HRID 2120198 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:14]=[C:13]2[C:9]([CH2:10][C:11](=[O:15])[NH:12]2)=[CH:8][CH:7]=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:2]3[S:1][CH:5]=[CH:4][CH:3]=3)=[CH:7][CH:8]=2)[NH:12][C:11]1=[O:15]

Participants

5

Reactant 3

HCID 6998SalicylaldehydeHCID 8082PiperidineHCID 219069896-Thiophen-2-yl-1,3-dihydro-indol-2-one

Product 1

HCID 538901693-(2-Hydroxybenzylidene)-6-thiophen-2-yl-1,3-dihydroindol-2-oneYield 50.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 6-thiophen-2-yl-1,3-dihydroindol-2-one (100 mg, 0.5 mmol), 2-hydroxybenzaldehyde (60 mg, 0.5 mmol) and piperidine (0.23 mL) in ethanol (4 mL) was stirred at reflux overnight. The reaction mixture was concentrated and column chromatographed (eluant—isopropanol/dichloromethane) to give 80 mg (50%) of 3-(2-hydroxybenzylidene)-6-thiophen-2-yl-1,3-dihydroindol-2-one as a yellow-orange solid.

Workup

  1. temperatureat reflux overnight
  2. concentrationThe reaction mixture was concentrated
  3. customcolumn chromatographed (eluant—isopropanol/dichloromethane)

Sources & evidence

ORD record
ord-2e57120d44044a998c0369582491fb23
Source dataset
uspto-grants-2004_02
Patent number
US06689806B1

Reaction notes

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