Water → 1,4-Dihydro-2,6-diphenyl-4-oxo-1(2,2,6,6-tetramethyl-4-piperidinyl)-3-pyridinecarboxylic acid

HRID 464766

反応式

HRID 464766 の反応式
[C:1]1([CH3:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[O:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]1=[O:14].[NH2:15][CH:16]1[CH2:21][C:20]([CH3:23])([CH3:22])[NH:19][C:18]([CH3:25])([CH3:24])[CH2:17]1.[OH2:26]>>[C:1]1([C:7]2[N:15]([CH:16]3[CH2:17][C:18]([CH3:25])([CH3:24])[NH:19][C:20]([CH3:23])([CH3:22])[CH2:21]3)[C:13]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[CH:12][C:11](=[O:26])[C:10]=2[C:9]([OH:8])=[O:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

参加物

5

反応物 4

HCID 962Water2 回HCID 1140TolueneHCID 375244-Amino-2,2,6,6-tetramethylpiperidineHCID 681542H-Pyran-2-one

生成物 1

HCID 202625531,4-Dihydro-2,6-diphenyl-4-oxo-1(2,2,6,6-tetramethyl-4-piperidinyl)-3-pyridinecarboxylic acid

実験手順

A 250 ml round-bottom flask is equipped with a mechanical stirrer, thermometer, and a distillation head and condenser set up to remove distillate. The flask is charged with 100 g (0.52 moles) ethyl benzoylacetate and 0.075 g sodium bicarbonate. The flask and its contents are heated by means of an oil bath over a period of about 5 hours at temperature from ambient to a maximum of 200° C. while the ethanol formed is continuously removed. Unreacted ethyl benzoylacetate is removed by vaccum distillation. The residue consisting of crude 3-benzoyl-6-phenyl-2H-pyran-2,4-(3H)-dione is then heated at 80°-85° C. with 500 g of 85% sulfuric acid for 4 hours. This mixture is poured into 1 liter of ice-water and the water extracted three times with 150 ml portions of chloroform. The combined chloroform extracts are stripped of volatiles on a rotary evaporator and the residue of 2,6-diphenyl-4-oxopyran-3-carboxylic acid isolated by fractional crystallization. A toluene solution of this pyrone is then treated with an equal molar quantity of 4-amino-2,2,6,6-tetramethylpiperidine and refluxed with removal of water by means of a Dean-Stark trap. When water has ceased to separate, the toluene is removed on a rotary evaporator and the residue cooled and treated with hexane to promote crystallization of the crude product. The product is further purified by fractional crystallization.

後処理

  1. customto separate
  2. customthe toluene is removed on a rotary evaporator
  3. temperaturethe residue cooled
  4. additiontreated with hexane
  5. customcrystallization of the crude product
  6. customThe product is further purified by fractional crystallization

出典と根拠

ORDレコード
ord-41116c427fb34e80995320712b996201
出典データセット
uspto-grants-1985_10
特許番号
US04548973

関連ノート

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