Benzyl Bromide → 5-Acetyl-8-(benzyloxy)-1,2-dihydroquinolin-2-one

HRID 1518613Notes

Reaction equation

HRID 1518613 reaction equation
[C:1]([C:4]1[CH:13]=[CH:12][C:11]([OH:14])=[C:10]2[C:5]=1[CH:6]=[CH:7][C:8](=[O:15])[NH:9]2)(=[O:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH2:22](Br)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CN(C)C=O>[C:1]([C:4]1[CH:13]=[CH:12][C:11]([O:14][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[C:10]2[C:5]=1[CH:6]=[CH:7][C:8](=[O:15])[NH:9]2)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 119838955-Acetyl-8-hydroxy-2(1H)-quinolinone

Product 1

HCID 133754445-Acetyl-8-(benzyloxy)-1,2-dihydroquinolin-2-oneYield 87.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-Acetyl-8-hydroxy-1H-quinolin-2-one (430 g, 2.12 mol) was suspended in N,N-dimethylformamide (3.3 L), potassium carbonate (298 g, 2.16 mol) and subsequently benzyl bromide (298 g, 2.11 mol) were added thereto, and the mixture was stirred at room temperature for 2 hours. The insoluble matter was removed by filtration and washed with N,N-dimethylformamide. The filtrate and the washing were mixed and concentrated under reduced pressure. To the residue was added purified water (3.3 L) and the mixture was stirred at room temperature overnight. The precipitate was collected by filtration, washed with purified water, and dried under vacuum to obtain 5-acetyl-8-benzyloxy-1H-quinolin-2-one (541 g).

Workup

  1. customThe insoluble matter was removed by filtration
  2. washwashed with N,N-dimethylformamide
  3. additionThe filtrate and the washing were mixed
  4. concentrationconcentrated under reduced pressure
  5. additionTo the residue was added
  6. custompurified water (3.3 L)
  7. stirringthe mixture was stirred at room temperature overnight
  8. filtrationThe precipitate was collected by filtration
  9. washwashed with purified water
  10. customdried under vacuum

Sources & evidence

ORD record
ord-5716d326ab464fea9688467c459fe100
Source dataset
uspto-grants-2015_07
Patent number
US09072734B2

Reaction notes

Loading…