7-Bromo-1-Chloroisoquinoline → 7-Bromo-1-butylisoquinoline

HRID 349055

Reaction equation

HRID 349055 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][N:8]=[C:9]2Cl)=[CH:4][CH:3]=1.[CH2:13]([Mg]Cl)[CH2:14][CH2:15][CH3:16]>C(OCC)C.C(OCC)(=O)C>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][N:8]=[C:9]2[CH2:13][CH2:14][CH2:15][CH3:16])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 65020247-Bromo-1-ChloroisoquinolineHCID 178418265HCID 178418265, compound

Product 1

HCID 210859957-Bromo-1-butylisoquinolineYield 24.4%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a refluxing solution of 7-bromo-1-chloroisoquinoline (4.85 g, 23.28 mmol) in diethyl ether (75 mL) was added butylmagnesium chloride (17.8 mL, 2.0 M ether, 35.6 mmol) and the reaction maintained at reflux for 2 h. The reaction mixture was cooled to room temperature, carefully diluted with an equal volume of ethyl acetate, washed with saturated sodium bicarbonate, water, and saturated sodium chloride, dried (sodium sulfate), filtered, and concentrated under reduced pressure to give an brown oil. Purification by flash column chromatography (silica, 1–10% ether/hexanes) gave the desired 7-bromo-1-butylisoquinoline (1.50 g): ESI MS m/z 264 [M+H]+.

Workup

  1. temperaturethe reaction maintained
  2. temperatureat reflux for 2 h
  3. washwashed with saturated sodium bicarbonate, water, and saturated sodium chloride
  4. dry with materialdried (sodium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto give an brown oil
  8. customPurification by flash column chromatography (silica, 1–10% ether/hexanes)

Sources & evidence

ORD record
ord-08c206c12c7d441bac3b2682a3e116dc
Source dataset
uspto-grants-2007_02
Patent number
US07176242B2

Linked notes

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