Salicylaldehyde → HCID 69883404, compound

HRID 2120196Notes

Reaction equation

HRID 2120196 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:15]=[C:14]3[C:10]([CH2:11][C:12](=[O:16])[NH:13]3)=[CH:9][CH:8]=2)[CH:2]=1.[OH:17][C:18]1[CH:25]=[CH:24][CH:23]=[CH:22][C:19]=1[CH:20]=O.N1CCCCC1>C(O)C>[OH:17][C:18]1[CH:25]=[CH:24][CH:23]=[CH:22][C:19]=1[CH:20]=[C:11]1[C:10]2[C:14](=[CH:15][C:7]([C:3]3[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=3)=[CH:8][CH:9]=2)[NH:13][C:12]1=[O:16]

Participants

5

Reactant 3

HCID 6998SalicylaldehydeHCID 8082PiperidineHCID 219155796-Pyridin-3-yl-1,3-dihydro-indol-2-one

Product 1

HCID 69883404HCID 69883404, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 6-pyridin-3-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 heated to reflux and stirred overnight. The reaction mixture was concentrated and column chromatographed (eluant—isopropanol/dichloromethane) to give 100 mg (64%) of 3-(2-hydroxybenzylidene)-6-pyridin-3-yl-1,3-dihydroindol-2-one as a yellow solid.

Workup

  1. temperaturewas heated
  2. temperatureto reflux
  3. concentrationThe reaction mixture was concentrated
  4. customcolumn chromatographed (eluant—isopropanol/dichloromethane)

Sources & evidence

ORD record
ord-8a5b495b87da464ea773ada6b152fd0a
Source dataset
uspto-grants-2004_02
Patent number
US06689806B1

Reaction notes

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