Hydrochloric Acid → 2',4,4'-Trimethoxy-6'-(nicotinoyloxy)chalcone

HRID 364660

반응식

HRID 364660 반응식
[OH:1][C:2]1[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[C:16]([O:22][CH3:23])[C:3]=1[C:4](=[O:15])[CH:5]=[CH:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=1.Cl.[C:25](Cl)(=[O:32])[C:26]1[CH:31]=[CH:30][CH:29]=[N:28][CH:27]=1>N1C=CC=CC=1>[CH3:23][O:22][C:16]1[CH:17]=[C:18]([O:20][CH3:21])[CH:19]=[C:2]([O:1][C:25](=[O:32])[C:26]2[CH:31]=[CH:30][CH:29]=[N:28][CH:27]=2)[C:3]=1[C:4](=[O:15])[CH:5]=[CH:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=1

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 82604Nicotinoyl chlorideHCID 235736Flavokavain A

생성물 1

HCID 537115972',4,4'-Trimethoxy-6'-(nicotinoyloxy)chalcone수율 83%

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

A solution of 2'-hydroxy-4,4',6'-trimethoxychalcone (1 g) and hydrochloride of nicotinoyl chloride (0.6 g) in 20 ml of pyridine was stirred at room temperature for 4 hours. After removal of the solvent followed by addition of saturated aqueous sodium bicarbonate (50 ml) to the residue, the mixture was extracted with ethyl acetate (100 ml). The extract was washed with water, dried over Na2SO4 and evaporated under reduced pressure to give an oily residue. Crystallization from methanol/hexane gave 1.1 g (83% yield) of 2',4,4'-trimethoxy-6'-(nicotinoyloxy)chalcone as pale yellow needles; m.p. 55°-60° C.

후처리

  1. customAfter removal of the solvent
  2. additionfollowed by addition of saturated aqueous sodium bicarbonate (50 ml) to the residue
  3. extractionthe mixture was extracted with ethyl acetate (100 ml)
  4. washThe extract was washed with water
  5. dry with materialdried over Na2SO4
  6. customevaporated under reduced pressure
  7. customto give an oily residue
  8. customCrystallization from methanol/hexane

출처 및 근거

ORD 기록
ord-56af71c55d844fe89e0f759430afc0cc
출처 데이터셋
uspto-grants-1986_08
특허 번호
US04605674

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