7-Bromo-1-Chloroisoquinoline → 7-bromo-N-butyl-N-methylisoquinolin-1-amine

HRID 14262

Reaction equation

HRID 14262 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>CNCCCC>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][N:8]=[C:9]2[N:8]([CH2:7][CH2:6][CH2:5][CH3:4])[CH3:9])=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 65020247-Bromo-1-Chloroisoquinoline

Product 1

HCID 210859977-bromo-N-butyl-N-methylisoquinolin-1-amineYield 161.1%

Reagents, catalysts & solvents 1

HCID 8068N-MethylbutylamineSolvent

Procedure

A solution of 7-bromo-1-chloroisoquinoline (750 mg, 3.09 mmol) in N-methylbutylamine (7.0 mL) was heated at 65° C. in a sealed tube for 18 h. The reaction mixture was concentrated under reduced pressure. The residue was diluted with chloroform and washed with saturated sodium bicarbonate, dried (sodium sulfate), filtered, and concentrated under reduced pressure to yield a brown oil. Purification by flash column chromatography (silica, 3:1 hexanes/diethyl ether) provided 7-bromo-N-butyl-N-methylisoquinolin-1-amine (730 mg): ESI MS m/z 293 [M+H]+.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionThe residue was diluted with chloroform
  3. washwashed with saturated sodium bicarbonate
  4. dry with materialdried (sodium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto yield a brown oil
  8. customPurification by flash column chromatography (silica, 3:1 hexanes/diethyl ether)

Sources & evidence

ORD record
ord-d676ac49f1b945c79fc6cf197f9470f2
Source dataset
uspto-grants-2010_06
Patent number
US07727997B2

Linked notes

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