Bromine → 4-Bromo-1-hydroxyisoquinoline

HRID 1645913Notes

Reaction equation

HRID 1645913 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]=1.[Br:12]Br>C(Cl)Cl>[Br:12][C:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:2]([OH:1])=[N:3][CH:4]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 178517620HCID 178517620, compound

Product 1

HCID 3197724-Bromo-1-hydroxyisoquinolineYield 63.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 5.0 g (34.5 mmol) of 1-hydroxyisoquinoline in 100 ml of methylene chloride was added 6.0 g (37.7 mmol) of bromine in 20 ml of methylene chloride. The mixture was stirred for four hours, the solid was filtered and washed with methylene chloride. This solid was recrystallized from ethanol to give 4.9 g (63%) of the desired product; mp 245°-250° (dec).

Workup

  1. filtrationthe solid was filtered
  2. washwashed with methylene chloride
  3. customThis solid was recrystallized from ethanol

Sources & evidence

ORD record
ord-cc87d6c0494349718bfb06d317de5360
Source dataset
uspto-grants-1993_01
Patent number
US05177075

Reaction notes

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