Isoquinoline → 3-Bromoisoquinoline

HRID 1470478Notes

Reaction equation

HRID 1470478 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1.C1C(=O)N([Br:18])C(=O)C1>CC(O)=O>[Br:18][C:3]1[N:2]=[CH:1][C:10]2[C:5]([CH:4]=1)=[CH:6][CH:7]=[CH:8][CH:9]=2

Participants

4

Reactant 2

HCID 8405IsoquinolineHCID 67184N-bromobutanimide

Product 1

HCID 6409693-BromoisoquinolineYield 23.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

To a stirred solution of isoquinoline (24 g, 186 mmol) in AcOH (50 mL) was added NBS (36.2 g, 204.6 mmol) at RT and the reaction mixture was heated to 100° C. overnight. Then it was cooled to RT and concentrated under reduced pressure. The crude product obtained was purified by flash column chromatography (5% EtOAc:Hexanes) to furnish the title compound (9.2 g, 23.8%) as an oil.

Workup

  1. temperatureThen it was cooled to RT
  2. concentrationconcentrated under reduced pressure
  3. customThe crude product obtained
  4. customwas purified by flash column chromatography (5% EtOAc:Hexanes)

Sources & evidence

ORD record
ord-6871dfb3d3d54c43aed05506f4704b9a
Source dataset
uspto-grants-2015_04
Patent number
US09006442B2

Reaction notes

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