Bromine → 6-bromo-7,8-dihydro-5(6H)-quinolinone hydrobromide

HRID 34649

Reaction equation

HRID 34649 reaction equation
[N:1]1[C:10]2[CH2:9][CH2:8][CH2:7][C:6](=[O:11])[C:5]=2[CH:4]=[CH:3][CH:2]=1.[Br:12]Br>Br>[BrH:12].[Br:12][CH:7]1[CH2:8][CH2:9][C:10]2[N:1]=[CH:2][CH:3]=[CH:4][C:5]=2[C:6]1=[O:11]

Participants

4

Reactant 2

HCID 24408BromineHCID 30168115(6H)-Quinolinone, 7,8-dihydro-

Product 1

HCID 142338126-bromo-7,8-dihydro-5(6H)-quinolinone hydrobromideYield 159.7%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

To a warm solution of 5.00 g (33.52 mmol) of 7,8-dihydro-5(6H)-quinolinone, prepared in Example 1, in 25 ml of 48% hydrobromic acid, was added dropwise 6.0 g (37.54 mmol) of bromine. The solution was stirred at room temperature for 1 hour, then concentrated to a yellow-white solide. Recrystallization from absolute ethanol afforded 9.20 g (88.5%) of 6-bromo-7,8-dihydro-5(6H)-quinolinone hydrobromide as a white solid; mp 187°-189° C. (dec.).

Workup

  1. concentrationconcentrated to a yellow-white solide
  2. customRecrystallization from absolute ethanol

Sources & evidence

ORD record
ord-578f15fde49f44e9a6bdc0d4de33ef8b
Source dataset
uspto-grants-1988_08
Patent number
US04762843

Linked notes

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