Benzaldehyde → 8-(Phenylmethylidene)-5,6,7,8-tetrahydroquinoline

HRID 1825962Notes

Reaction equation

HRID 1825962 reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:9]1[C:18]2[CH2:17][CH2:16][CH2:15][CH2:14][C:13]=2[CH:12]=[CH:11][CH:10]=1>C(OC(=O)C)(=O)C>[CH:1](=[C:17]1[C:18]2[N:9]=[CH:10][CH:11]=[CH:12][C:13]=2[CH2:14][CH2:15][CH2:16]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 240BenzaldehydeHCID 663355,6,7,8-Tetrahydroquinoline

Product 1

HCID 540746508-(Phenylmethylidene)-5,6,7,8-tetrahydroquinolineYield 58%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

Benzaldehyde (3.59 mL, 35.30 mmole) was added to a solution of 5,6,7,8-tetrahydro-quinoline (4.70 g, 35.30 mmole) in acetic anhydride (25 mL), and the solution was heated to reflux under a nitrogen atmosphere. After overnight at reflux, the reaction was concentrated in vacuo. The residue was diluted with water and extracted with ethyl acetate. The combined organic extracts were washed with brine, dried over Na2SO4, and concentrated. The residue was purified by flash chromatography on silica gel (33% EtOAc/hexanes) to give the title compound (4.50 g, 58%) as a waxy yellow solid after drying in vacuo: MS (ES) m/e 222 (M+H)+.

Workup

  1. temperaturethe solution was heated
  2. temperatureto reflux under a nitrogen atmosphere
  3. temperatureAfter overnight at reflux
  4. concentrationthe reaction was concentrated in vacuo
  5. additionThe residue was diluted with water
  6. extractionextracted with ethyl acetate
  7. washThe combined organic extracts were washed with brine
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated
  10. customThe residue was purified by flash chromatography on silica gel (33% EtOAc/hexanes)

Sources & evidence

ORD record
ord-13bd91f7a4f044aeb734061931eda3cb
Source dataset
uspto-grants-2006_05
Patent number
US07049310B2

Reaction notes

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