7-Bromo-1-Chloroisoquinoline → 7-bromo-2-(N-propylamino)isoquinoline

HRID 14256

Reaction equation

HRID 14256 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]=1

Participants

3

Reactant 1

HCID 65020247-Bromo-1-Chloroisoquinoline

Product 1

HCID 210859967-bromo-2-(N-propylamino)isoquinoline

Reagents, catalysts & solvents 1

HCID 7852PropylamineSolvent

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

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutiondissolved in chloroform
  3. washwashed with saturated sodium bicarbonate, saturated sodium chloride
  4. dry with materialdried (sodium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d4e7541abda242baa613fc8098349853
Source dataset
uspto-grants-2010_06
Patent number
US07727997B2

Linked notes

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