4-(Dimethylamino)Benzaldehyde → HCID 67187758, compound

HRID 1965837Notes

Reaction equation

HRID 1965837 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[CH2:5]2.[CH3:12][N:13]([CH3:22])[C:14]1[CH:21]=[CH:20][C:17]([CH:18]=O)=[CH:16][CH:15]=1.N1CCCCC1>CCO>[CH3:12][N:13]([CH3:22])[C:14]1[CH:21]=[CH:20][C:17]([CH:18]=[C:5]2[C:4]3[C:8](=[CH:9][CH:10]=[C:2]([F:1])[CH:3]=3)[NH:7][C:6]2=[O:11])=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 74794-(Dimethylamino)BenzaldehydeHCID 8082PiperidineHCID 37310125-fluoro-1,3-dihydro-2H-indol-2-one

Product 1

HCID 67187758HCID 67187758, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A general procedure for the preparation of 3-benzylideneindolin-2-ones: A mixture of 5-fluoroindolin-2-one (151 mg, 1 mmol), 4-(dimethylamino)benzaldehyde (149 mg, 1 mmol), and piperidine (12.7 mg, 0.15 mmol) in 4 mL EtOH was heated at reflux for 15 h and cooled to rt. The solid was collected via filtration and washed with ether (10 mL), and dried under vacuum. The crude product was further purified with silica chromatography (hexane/EtOAc) to afford 3-(4-(dimethylamino)benzylidene)-5-fluoroindolin-2-one as a orange solid (220 mg, 78%, E/Z ratio 7:1). For the major E/Z isomer: 1H NMR (400 MHz, acetone-d6) δ 9.41 (s, 1 H), 7.68-7.64 (m, 3 H), 7.58 (dd, J=9.6, 2.4 Hz, 1 H), 6.98-6.86 (m, 4 H), 3.09 (s, 6 H); MS (ESI) m/z 283 (M+H+).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 15 h
  3. filtrationThe solid was collected via filtration
  4. washwashed with ether (10 mL)
  5. customdried under vacuum
  6. customThe crude product was further purified with silica chromatography (hexane/EtOAc)

Sources & evidence

ORD record
ord-d261533bb8ed42b38340e56243318452
Source dataset
uspto-grants-2013_04
Patent number
US08420052B2

Reaction notes

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