Water → 1-[8-(Benzyloxy)quinolin-5-yl]ethan-1-one
Reaction equation
Cl.[C:2]([C:5]1[CH:14]=[CH:13][C:12]([OH:15])=[C:11]2[C:6]=1[CH:7]=[CH:8][CH:9]=[N:10]2)(=[O:4])[CH3:3].C(=O)([O-])[O-].[K+].[K+].[CH2:22](Cl)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.O>CN(C)C=O>[C:2]([C:5]1[CH:14]=[CH:13][C:12]([O:15][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[C:11]2[C:6]=1[CH:7]=[CH:8][CH:9]=[N:10]2)(=[O:4])[CH3:3]Participants
Procedure
27 g of 5-acetyl-8-hydroxyquinoline hydrochloride are dissolved in 540 ml of anhydrous dimethylformamide and 50 g of powdered potassium carbonate are added thereto. 18.4 g of benzyl chloride are added to the mixture at 50° C. under an argon atmosphere, and the mixture is stirred at the same temperature for 4.5 hours and then further stirred at room temperature for 1.5 hours. After the reaction, water is added to the mixture, and the aqueous mixture is extracted with ethyl acetate. The extract is washed with water, a saturated sodium chloride solution, dried and then evaporated under reduced pressure to remove ethyl acetate. The residue is recrystallized from ethanol. 19.1 g of 5-acetyl-8-benzyloxyquinoline are obtained as brownish prisms. 6.35 g of said product are further recovered from the mother liquor.
Workup
- stirringfurther stirred at room temperature for 1.5 hours
- additionis added to the mixture
- extractionthe aqueous mixture is extracted with ethyl acetate
- washThe extract is washed with water
- dry with materiala saturated sodium chloride solution, dried
- customevaporated under reduced pressure
- customto remove ethyl acetate
- customThe residue is recrystallized from ethanol
Sources & evidence
- ORD record
- ord-99211616f59f4803bbd98015a4ae2dfd
- Source dataset
- uspto-grants-1986_04
- Patent number
- US04579854
Reaction notes
Loading…