Ethyl Acetate → 8-Ethyl-2-methylquinoline

HRID 338866Notes

Reaction equation

HRID 338866 reaction equation
[CH2:1]([C:3]1[CH:9]=[CH:8][CH:7]=[CH:6][C:4]=1[NH2:5])[CH3:2].[CH:10](=O)/[CH:11]=[CH:12]/[CH3:13].C(OCC)(=O)C>Cl>[CH2:1]([C:3]1[CH:9]=[CH:8][CH:7]=[C:6]2[C:4]=1[N:5]=[C:12]([CH3:13])[CH:11]=[CH:10]2)[CH3:2]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 113572-EthylanilineHCID 447466Crotonaldehyde

Product 1

HCID 144752508-Ethyl-2-methylquinolineYield 59.1%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 2-ethylaniline (4.00 g, 33.0 mmol) in 6 N HCl (40 mL) was added (E)-but-2-enal (6.20 ml, 75.9 mmol) dropwise at reflux. The reaction was heated at reflux for 3 hours. After cooling to ambient temperature, ethyl acetate (40 mL) was added. The aqueous layer was separated, basified with ammonium hydroxide to about pH 9, and extracted with DCM (2×50 mL). The combined organic layer was dried (sodium sulfate) and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (3:1 hexane/DCM) to give 8-ethyl-2-methylquinoline (3.34 g, 59.1%) as a solid.

Workup

  1. temperatureat reflux
  2. temperatureThe reaction was heated
  3. temperatureat reflux for 3 hours
  4. customThe aqueous layer was separated
  5. extractionextracted with DCM (2×50 mL)
  6. dry with materialThe combined organic layer was dried (sodium sulfate)
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by flash chromatography on silica gel (3:1 hexane/DCM)

Sources & evidence

ORD record
ord-8396065af8ef454ba60fc6a8f343bfe7
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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