Sodium Chloride → 5-Acetyl-8-(benzyloxy)-1,2-dihydroquinolin-2-one

To the product of step (b) (37.7 g, 186 mmol) was added N,N-dimethylformamide (200 mL) and potassium carbonate (34.5 g, 250 mmol) followed by benzyl bromide (31.8 g, 186 mmol). The mixture was stirred at room temperature for 2.25 hour and then poured into saturated sodium chloride (3.5 L) at 0° C. and stirred for 1 hour. The product was collected and dried on a Buchner funnel for 1 hour, and the resulting solids were dissolved in dichloromethane (2 L) and this mixture was dried over sodium sulfate. The solution was filtered through a pad of Celite which was then washed with dichloromethane (5×200 mL). The combined filtrate was then concentrated to dryness and the resulting solids were triturated with ether (500 mL) for 2 h. The product was collected on a Buchner funnel, washed with ether (2×250 mL) and dried under reduced pressure to give 5-acetyl-8-benzyloxy-1H-quinolin-2-one (44 g) as a powder.

1. stirringstirred for 1 hour
2. customThe product was collected
3. customdried on a Buchner funnel for 1 hour
4. dissolutionthe resulting solids were dissolved in dichloromethane (2 L)
5. dry with materialthis mixture was dried over sodium sulfate
6. filtrationThe solution was filtered through a pad of Celite which
7. washwas then washed with dichloromethane (5×200 mL)
8. concentrationThe combined filtrate was then concentrated to dryness
9. customthe resulting solids were triturated with ether (500 mL) for 2 h
10. customThe product was collected on a Buchner funnel
11. washwashed with ether (2×250 mL)
12. customdried under reduced pressure

ORD record

ord-96d2916b87d547bd8154efc7dc12ea46

Source dataset

uspto-grants-2006_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07141671B2