Sulfuric Acid → Phenethyl 2-phenyl-4-quinolone-6-carboxylate

HRID 986240Notes

Reaction equation

HRID 986240 reaction equation
[C:1]1([C:7]2[CH2:16][C:15](=[O:17])[C:14]3[C:9](=[CH:10][CH:11]=[C:12]([C:18]([OH:20])=[O:19])[CH:13]=3)[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:21](O)[CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.S(=O)(=O)(O)O.CCOCC>C(O)C.O>[C:1]1([C:7]2[CH2:16][C:15](=[O:17])[C:14]3[C:9](=[CH:10][CH:11]=[C:12]([C:18]([O:20][CH2:21][CH2:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)=[O:19])[CH:13]=3)[N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 3283Diethyl EtherHCID 60542-PhenylethanolHCID 704325112-Phenyl-4-quinolone-6-carboxylic acid

Product 1

HCID 70433061Phenethyl 2-phenyl-4-quinolone-6-carboxylate

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

2-Phenyl-4-quinolone-6-carboxylic acid (1.5 grams) obtained in Example 2 is stirred for fifteen hours at 110° C. with 50 ml of phenethyl alcohol and 1 ml of concentrated sulfuric acid. After cooling, 1.5 liters of ether is added to the mixture, the mixture is cooled with ice, oil which separates out therefrom is taken out. The mixture is then dissolved in 5 ml of ethanol. Then 3 ml of water is added thereto, and crystal which separates out therefrom are collected by filtration, and washed with a 5% sodium bicarbonate solution, then with water, and finally with methanol, and dried to give 0.9 gram of phenethyl 2-phenyl-4-quinolone-6-carboxylate, colorless powder, melting point 282°to 284° C.

Workup

  1. temperatureAfter cooling
  2. temperaturethe mixture is cooled with ice, oil which
  3. filtrationout therefrom are collected by filtration
  4. washwashed with a 5% sodium bicarbonate solution
  5. dry with materialwith water, and finally with methanol, and dried

Sources & evidence

ORD record
ord-72ad812d11134cfe8a5b689d76b38e02
Source dataset
uspto-grants-1987_12
Patent number
US04711898

Reaction notes

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