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

HRID 364657

Reaction equation

HRID 364657 reaction equation
[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

Participants

6

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 66654XanthoxylinHCID 739424-Acetamidobenzaldehyde

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-1210839f15c84e60a525e0196f7a6b40
Source dataset
uspto-grants-1986_08
Patent number
US04605674

Linked notes

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