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

HRID 364660

Reaction equation

HRID 364660 reaction equation
[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

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 82604Nicotinoyl chlorideHCID 235736Flavokavain A

Product 1

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

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-56af71c55d844fe89e0f759430afc0cc
Source dataset
uspto-grants-1986_08
Patent number
US04605674

Linked notes

Loading…