Aluminum(III) Chloride → 6-Bromo-1,2,3,4-tetrahydroquinoline

HRID 2301954Notes

Reaction equation

HRID 2301954 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH2:7][C:6](=O)[CH2:5]2.[Cl-].[Cl-].[Cl-].[Al+3].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1.C(=O)([O-])[O-].[Na+].[Na+]>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH2:7][CH2:6][CH2:5]2

Participants

6

Reactant 3

HCID 6451240Aluminum(III) ChlorideHCID 121488316-bromo-2,3-dihydro-1H-quinolin-3-oneHCID 21226445Aluminium lithium hydride

Product 1

HCID 47150296-Bromo-1,2,3,4-tetrahydroquinolineYield 87%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 10340Sodium CarbonateSolvent

Procedure

A solution of 6-bromo-2,3-dihydro-1H-quinolin-3-one (0.05 g, 0.219 mmol) in THF (20 mL) and aqueous sodium carbonate (5 mL) was treated with aluminum trichloride (0.116 g, 0.9 mmol) and lithium aluminum hydride (33 mg, 0.9 mmol) The reaction was refluxed for 18 h. and cooled down. The filtrate evaporated to dryness, taken up in water and extracted with EtOAc (3×). Ethyl acetate extracts were dried over sodium sulfate and concentrated. The crude residue was purified by flash chromatography (hexane/EtOAc, 1:3) to afford 6-bromo-2,3-dihydro-1H-quinoline (0.040 g, 87%). LRMS (ES+): 211.3 (M+H)+.

Workup

  1. temperaturewas refluxed for 18 h.
  2. temperaturecooled down
  3. customThe filtrate evaporated to dryness
  4. extractionextracted with EtOAc (3×)
  5. dry with materialEthyl acetate extracts were dried over sodium sulfate
  6. concentrationconcentrated
  7. customThe crude residue was purified by flash chromatography (hexane/EtOAc, 1:3)

Sources & evidence

ORD record
ord-dc8c6f88d7b1418493d7f7718610087c
Source dataset
uspto-grants-2002_08
Patent number
US06429205B1

Reaction notes

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