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

To a suspension of 5-acetyl-8-(benzyloxy)quinolin-2(1H)-one (19.4 g, 66.4 mmol) in anhydrous THF (240 mL) and anhydrous methanol (165 mL) was added a solution of tetra-n-butylammonium tribromide (54.5 g, 113.0 mmol) in anhydrous THF (130 mL) dropwise over 1.5 hours. The resulting solution was stirred at RT overnight before concentrating under reduced pressure without heating. The residue was re-dissolved in methanol (200 mL). Saturated aqueous ammonium chloride solution (390 mL) was added with ice-cooling. The resulting suspension was filtered, and the solid washed with water and air-dried under vacuum. The solid was suspended in DCM and methanol (1:1 v/v, 100 mL) for 90 minutes. The solid was collected by filtration, washed with DCM and air-dried to afford the title compound (18.0 g, 73%).

1. concentrationbefore concentrating under reduced pressure
2. temperaturewithout heating
3. dissolutionThe residue was re-dissolved in methanol (200 mL)
4. additionSaturated aqueous ammonium chloride solution (390 mL) was added with ice-
5. temperaturecooling
6. filtrationThe resulting suspension was filtered
7. washthe solid washed with water
8. customair-dried under vacuum
9. waitmethanol (1:1 v/v, 100 mL) for 90 minutes
10. filtrationThe solid was collected by filtration
11. washwashed with DCM
12. customair-dried

ORD-Eintrag

ord-7f5f73ac0f58484d8c90f3d9d86f6a45

Quelldatensatz

uspto-grants-2014_11

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08877774B2