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

HRID 1361965Notes

Reaction equation

HRID 1361965 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-4268f1cf67894afba6df4a72cce38052
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Reaction notes

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