Bromine → 4-Bromo-5-methylisoquinolin-1(2H)-one

HRID 1645914Notes

Reaction equation

HRID 1645914 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][NH:6][C:7]2=[O:12].[Br:13]Br>C(Cl)Cl.CCOCC>[Br:13][C:4]1[C:3]2[C:8](=[CH:9][CH:10]=[CH:11][C:2]=2[CH3:1])[C:7](=[O:12])[NH:6][CH:5]=1

Participants

5

Reactant 2

HCID 24408BromineHCID 99204505-Methyl-1,2-dihydroisoquinolin-1-one

Product 1

HCID 183694934-Bromo-5-methylisoquinolin-1(2H)-oneYield 29%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a suspension of 0.8 g (5.0 mmol) of 5-methyl-1-isoquinolinone in 30 ml of methylene chloride was added 0.85 (5.3 mmol) of bromine. The resulting orange mixture was stirred at 25° for 18 hours and diluted with 50 ml of ether. The solid was filtered and washed with methanol to give 0.35 g (29%) of product; mp 201°-210°.

Workup

  1. filtrationThe solid was filtered
  2. washwashed with methanol

Sources & evidence

ORD record
ord-9ab914f771d14422979e6d0854d8d22a
Source dataset
uspto-grants-1993_01
Patent number
US05177075

Reaction notes

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