Pyridiniumtribromide → HCID 86662509, compound

HRID 1518640Notes

Reaction equation

HRID 1518640 reaction equation
[C:1]([C:4]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)=[C:10]2[C:5]=1[CH:6]=[CH:7][C:8](=[O:24])[NH:9]2)(=[O:3])[CH3:2].[Br-:25].[Br-].[Br-].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>O1CCCC1>[Br:25][CH2:2][C:1]([C:4]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]2[CH:17]=[CH:18][C:19]([O:22][CH3:23])=[CH:20][CH:21]=2)=[C:10]2[C:5]=1[CH:6]=[CH:7][C:8](=[O:24])[NH:9]2)=[O:3]

Participants

4

Reactant 2

HCID 21124087PyridiniumtribromideHCID 66596969HCID 66596969, compound

Product 1

HCID 86662509HCID 86662509, compoundYield 33.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

5-Acetyl-8-[(4-methoxyphenyl)methoxy]-1,2-dihydroquinolin-2-one (1.25 g, 3.87 mmol) was dissolved in tetrahydrofuran (10 mL) and the solution was cooled to 0° C. Pyridinium tribromide (1.51 g, 4.25 mmol) was added in portions thereto and the reaction mixture was heated under reflux overnight. The precipitate was collected by filtration and washed with tetrahydrofuran. The filtrate was concentrated under reduced pressure and, thereafter, the residue was suspension-washed with purified water (20 mL). The precipitate was collected by filtration and washed with purified water. The solid was suspension-washed with ethyl acetate (20 mL), collected by filtration, and dried under reduced pressure to obtain 5-(2-bromoacetyl)-8-[(4-methoxyphenyl)methoxy]-1,2-dihydroquinolin-2-one (515 mg).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureunder reflux overnight
  3. filtrationThe precipitate was collected by filtration
  4. washwashed with tetrahydrofuran
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. washthe residue was suspension-washed with purified water (20 mL)
  7. filtrationThe precipitate was collected by filtration
  8. washwashed with purified water
  9. washThe solid was suspension-washed with ethyl acetate (20 mL)
  10. filtrationcollected by filtration
  11. customdried under reduced pressure

Sources & evidence

ORD record
ord-973ea9e53b9a48198face942c0e6fa1a
Source dataset
uspto-grants-2015_07
Patent number
US09072734B2

Reaction notes

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