Water → 4-Amino-2'-hydroxy-4',6'-dimethoxychalcone

HRID 364657

반응식

HRID 364657 반응식
[OH:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[C:4]([O:10][CH3:11])[C:3]=1[C:12](=[O:14])[CH3:13].C([NH:18][C:19]1[CH:26]=[CH:25][C:22]([CH:23]=O)=[CH:21][CH:20]=1)(=O)C.[OH-].[K+].O>C(O)C>[NH2:18][C:19]1[CH:26]=[CH:25][C:22]([CH:23]=[CH:13][C:12]([C:3]2[C:4]([O:10][CH3:11])=[CH:5][C:6]([O:8][CH3:9])=[CH:7][C:2]=2[OH:1])=[O:14])=[CH:21][CH:20]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 66654XanthoxylinHCID 739424-Acetamidobenzaldehyde

생성물 1

HCID 538157474-Amino-2'-hydroxy-4',6'-dimethoxychalcone수율 8%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A mixture of 98 mg of 2'-hydroxy-4',6'-dimethoxyacetophenone, 85 mg of 4-acetamidobenzaldehyde and 1 g of potassium hydroxide in 4 ml of 50% aqueous ethanol was stirred at room temperature for 3 days. The mixture was poured into 30 ml of cold water and then extracted with three 30 ml portions of ethyl acetate. The combined extracts were washed with water, dried over anhydrous sodium sulfate and evaporated under reduced pressure. The residue was purified by preparative thin layer chromatography using a silica gel plate (Kiesel gel 60 F254, Merck Co.) and cyclohexane/ethyl acetate (1:1, v/v) as the developing solvent, whereby 12 mg of 4-amino-2'-hydroxy-4',6'-dimethoxychalcone as a yellow powder were obtained: Rf value 0.22; 1H-nmr spectrum (in CDCl3): δ3.6(2H), 3.72(3H), 3.82(3H), 5.90(1H), 6.06(1H), 6.56(1H), 6.70(1H), 7.50(1H), 7.62(1H) and 14.4 ppm (1H).

후처리

  1. extractionextracted with three 30 ml portions of ethyl acetate
  2. washThe combined extracts were washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. customevaporated under reduced pressure
  5. customThe residue was purified by preparative thin layer chromatography

출처 및 근거

ORD 기록
ord-1210839f15c84e60a525e0196f7a6b40
출처 데이터셋
uspto-grants-1986_08
특허 번호
US04605674

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