Water → 1-[8-(Benzyloxy)quinolin-5-yl]ethan-1-one

HRID 1722600노트

반응식

HRID 1722600 반응식
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]

참가 물질

6

반응물 4

HCID 962WaterHCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 200268805-Acetyl-8-hydroxyquinoline hydrochloride

생성물 1

HCID 137448911-[8-(Benzyloxy)quinolin-5-yl]ethan-1-one수율 57.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  1. stirringfurther stirred at room temperature for 1.5 hours
  2. additionis added to the mixture
  3. extractionthe aqueous mixture is extracted with ethyl acetate
  4. washThe extract is washed with water
  5. dry with materiala saturated sodium chloride solution, dried
  6. customevaporated under reduced pressure
  7. customto remove ethyl acetate
  8. customThe residue is recrystallized from ethanol

출처 및 근거

ORD 기록
ord-a4400198f1a34552a552f4f1136d4bbd
출처 데이터셋
uspto-grants-1989_08
특허 번호
USRE033024

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