Potassium Carbonate → HCID 66596969, compound

HRID 1518639Notes

Reaction equation

HRID 1518639 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+].[CH3:22][O:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28]Cl)=[CH:26][CH:25]=1>CN(C)C=O>[C:1]([C:4]1[CH:13]=[CH:12][C:11]([O:14][CH2:28][C:27]2[CH:30]=[CH:31][C:24]([O:23][CH3:22])=[CH:25][CH:26]=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 11430Potassium CarbonateHCID 699934-Methyloxybenzyl chlorideHCID 119838955-Acetyl-8-hydroxy-2(1H)-quinolinone

Product 1

HCID 66596969HCID 66596969, compoundYield 53.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

5-Acetyl-8-hydroxy-1H-quinolin-2-one (29.5 g, 0.15 mol) was suspended in N,N-dimethylformamide (145 mL), potassium carbonate (22.2 g, 0.16 mol) and successively 4-methoxybenzyl chloride (22.7 g, 0.15 mol) were added thereto, and the mixture was stirred at 90° C. overnight. To the reaction mixture was added purified water (0.5 L) and the mixture was stirred at room temperature overnight. The precipitate was collected by filtration, washed with purified water, dried under reduced pressure to obtain 5-acetyl-8-[(4-methoxyphenyl)methoxy]-1,2-dihydroquinolin-2-one (26.1 g).

Workup

  1. additionTo the reaction mixture was added
  2. custompurified water (0.5 L)
  3. stirringthe mixture was stirred at room temperature overnight
  4. filtrationThe precipitate was collected by filtration
  5. washwashed with purified water
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-72683aafa728470ea560b7a837fa0a00
Source dataset
uspto-grants-2015_07
Patent number
US09072734B2

Reaction notes

Loading…