Potassium Hydroxide → HCID 19972722, compound

HRID 1452305Notes

Reaction equation

HRID 1452305 reaction equation
[CH:1]([C:3]1[C:12]2[O:11][CH:10]=[C:9]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:8](=[O:19])[C:7]=2[CH:6]=[CH:5][CH:4]=1)=[O:2].[OH-:20].[K+]>O.C(O)C.CN(C)C=O.[N+]([O-])([O-])=O.[Ag+]>[C:1]([C:3]1[C:12]2[O:11][CH:10]=[C:9]([C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:8](=[O:19])[C:7]=2[CH:6]=[CH:5][CH:4]=1)([OH:20])=[O:2]

Participants

7

Reactant 2

HCID 14797Potassium HydroxideHCID 13324415HCID 13324415, compound

Product 1

HCID 19972722HCID 19972722, compound

Reagents, catalysts & solvents 4

HCID 24470Silver NitrateCatalystHCID 702EthanolSolventHCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Procedure

A solution of 38.22 g of silver nitrate in 75 ml of water was added dropwise, under stirring, at 20°-25° C., to a solution of 22.5 g of 8-formyl-4-oxo-3-phenyl-4H-1-benzopyran (prepared as described by G. Atassi et al., Eur. J. Med. Chem. - Chim. Ter. 20, 393 (1985)) in 150 ml of 85% ethanol and 450 ml of N,N-dimethylformamide. Then, a solution of 32.67 g of 85% potassium hydroxide in 195 ml of water was added dropwise under stirring at 15°-20° C. After additional stirring at room temperature, the reaction mixture was filtered by suction; the mother liquor was acidified with 37% hydrochloric acid and diluted with 1.2 l of water. Filtration by suction and washing with water to neutrality gave the title compound as a crude. The crude was suspended in 150 ml of ethyl acetate and stirred with 444 ml of 0.3M aqueous sodium hydrogen carbonate solution until clear layers were obtained. The aqueous layer was washed with 75 ml of ethyl acetate, then made acidic with 37% hydrochloric acid, filtered and dried at 60°-65° C. to give 19, 12 g of the title compound that melted at (215) 218° C. A sample, crystallized from ethanol, showed the same melting point, m.p. (215) 218° C.

Workup

  1. stirringAfter additional stirring at room temperature
  2. filtrationthe reaction mixture was filtered by suction
  3. additiondiluted with 1.2 l of water
  4. filtrationFiltration by suction
  5. washwashing with water to neutrality

Sources & evidence

ORD record
ord-f94a1b1ae2c544d3bcccfcc424155694
Source dataset
uspto-grants-1997_02
Patent number
US05605896

Reaction notes

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