N-bromobutanimide → 4-Bromo-1-hydroxyisoquinoline

HRID 2289825Notes

Reaction equation

HRID 2289825 reaction equation
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][C:8](S(Cl)(=O)=O)=[CH:9][CH:10]=2)[C:5](Cl)=[N:4][CH:3]=1.C1([OH:27])C2C(=CC=CC=2)C=CN=1.BrN1C(=O)CCC1=O>CC#N>[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](=[O:27])[NH:4][CH:3]=1

Participants

5

Reactant 3

HCID 67184N-bromobutanimideHCID 186984014-Bromo-1-chloro-7-isoquinolinesulphonyl chlorideHCID 178517620HCID 178517620, compound

Product 1

HCID 3197724-Bromo-1-hydroxyisoquinoline

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-Bromo-1-chloro-7-isoquinolinesulphonyl chloride ##STR198## A suspension of isoquinolinol (10 g, 68.9 mmol) in MeCN (250 ml) at 50° C., was treated with N-bromosuccinimide (12.6 g, 70.8 mmol) whereupon almost complete solution occurred before a thick white precipitate was formed. After heating under reflux for 3 h, the reaction mixture was cooled in ice and the solid filtered, washed with MeCN, and dried to afford 4-bromo-1-(2H)-isoquinolone (7.6 g, 34.0 mmol).

Workup

  1. customwas formed
  2. temperatureAfter heating
  3. temperatureunder reflux for 3 h
  4. temperaturethe reaction mixture was cooled in ice
  5. filtrationthe solid filtered
  6. washwashed with MeCN
  7. customdried

Sources & evidence

ORD record
ord-b0f146c8ff934f41aee8bfff8e9c916c
Source dataset
uspto-grants-2000_07
Patent number
US06093731

Reaction notes

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