7-Bromo-1-Chloroisoquinoline → 7-bromo-2-(N-propylamino)isoquinoline
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>C(N)CC>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][N:8]([NH:8][CH2:7][CH2:6][CH3:5])[CH2:9]2)=[CH:4][CH:3]=1Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 7-bromo-1-chloroisoquinoline in propylamine (15.0 mL) was heated at 70° C. in a sealed tube overnight. The reaction mixture was concentrated under reduced pressure, then dissolved in chloroform and washed with saturated sodium bicarbonate, saturated sodium chloride, dried (sodium sulfate), filtered, and concentrated under reduced pressure to yield 7-bromo-2-(N-propylamino)isoquinoline (820 mg): ESI MS m/z 266 [M+H]+.
Workup
- concentrationThe reaction mixture was concentrated under reduced pressure
- dissolutiondissolved in chloroform
- washwashed with saturated sodium bicarbonate, saturated sodium chloride
- dry with materialdried (sodium sulfate)
- filtrationfiltered
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-d4e7541abda242baa613fc8098349853
- Source dataset
- uspto-grants-2010_06
- Patent number
- US07727997B2
Reaction notes
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