5-Acetyl-8-(benzyloxy)-1,2-dihydroquinolin-2-one → 8-Benzyloxy-5-(2-bromoacetyl)-2-hydroxyquinoline

HRID 1518614Notes

Reaction equation

HRID 1518614 reaction equation
[C:1]([C:4]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:10]2[C:5]=1[CH:6]=[CH:7][C:8](=[O:22])[NH:9]2)(=[O:3])[CH3:2].[Br-:23].[Br-].[Br-].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>O1CCCC1>[CH2:15]([O:14][C:11]1[CH:12]=[CH:13][C:4]([C:1](=[O:3])[CH2:2][Br:23])=[C:5]2[C:10]=1[NH:9][C:8](=[O:22])[CH:7]=[CH:6]2)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 133754445-Acetyl-8-(benzyloxy)-1,2-dihydroquinolin-2-oneHCID 21124087Pyridiniumtribromide

Product 1

HCID 116678678-Benzyloxy-5-(2-bromoacetyl)-2-hydroxyquinolineYield 81.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

5-Acetyl-8-benzyloxy-1H-quinolin-2-one (372 g, 1.27 mol) was dissolved in tetrahydrofuran (3.6 L) and the solution was cooled to 0° C. Pyridinium tribromide (453 g, 1.27 mol) was added thereto in portions, and the mixture was heated under reflux for 3 hours. Thereafter, tetrahydrofuran (3.1 L) was added and the mixture was heated under reflux overnight. The precipitate was collected by filtration and washed with tetrahydrofuran. The solid was suspension-washed with tetrahydrofuran (2.3 L) and, thereafter, washed with purified water (3 L). Separately, the tetrahydrofuran filtrate and the washings were mixed, concentrated under reduced pressure, and the residue was suspension-washed with tetrahydrofuran (1 L). The solids were combined and dried under reduced pressure to obtain 8-benzyloxy-5-(2-bromoacetyl)-1H-quinolin-2-one (387 g).

Workup

  1. temperaturein portions, and the mixture was heated
  2. temperatureunder reflux for 3 hours
  3. temperaturethe mixture was heated
  4. temperatureunder reflux overnight
  5. filtrationThe precipitate was collected by filtration
  6. washwashed with tetrahydrofuran
  7. washThe solid was suspension-washed with tetrahydrofuran (2.3 L)
  8. washwashed with purified water (3 L)
  9. additionSeparately, the tetrahydrofuran filtrate and the washings were mixed
  10. concentrationconcentrated under reduced pressure
  11. washthe residue was suspension-washed with tetrahydrofuran (1 L)
  12. customdried under reduced pressure

Sources & evidence

ORD record
ord-c2b35190570d45558ed5ca3ab7c1e6ad
Source dataset
uspto-grants-2015_07
Patent number
US09072734B2

Reaction notes

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