Gamma-Butyrolactone → 4-hydroxy-3-(2-hydroxyethyl)-1-phenyl-1,8-naphthyridin-2(1H)-one

HRID 1583314ノート

反応式

HRID 1583314 の反応式
[C:1]1([NH:7][C:8]2[C:13]([C:14]([O:16]C)=O)=[CH:12][CH:11]=[CH:10][N:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:18]1(=[O:23])[O:22][CH2:21][CH2:20][CH2:19]1.CC(C)([O-])C.[K+]>>[OH:23][CH2:18][CH2:19][C:20]1[C:21](=[O:22])[N:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:8]2[C:13]([C:14]=1[OH:16])=[CH:12][CH:11]=[CH:10][N:9]=2

参加物

4

反応物 3

HCID 7302Gamma-ButyrolactoneHCID 10998755Methyl 2-anilinopyridine-3-carboxylateHCID 23665647Potassium tert-butoxide

生成物 1

HCID 547236674-hydroxy-3-(2-hydroxyethyl)-1-phenyl-1,8-naphthyridin-2(1H)-one

反応条件

温度
95 °C

実験手順

To a solution of 6.8 g. of methyl 2-phenylamino-3-pyridine carboxylate in 60 ml. of gammabutyrolactone there is added, under nitrogen, 13.4 g. of potassium tertiary butoxide. The reaction mixture is heated and stirred for one hour at 95° C., poured on ice and stirred overnite. The mixture is extracted with ether, the aqueous layer acidified with acetic acid to pH 4.5 and the product is collected by filtration. Recrystallization from chloroform, acetone, isopropanol yields the product of this example as a colorless solid; m.p. 235°-236° C.

後処理

  1. temperatureThe reaction mixture is heated
  2. additionpoured on ice
  3. stirringstirred overnite
  4. extractionThe mixture is extracted with ether
  5. filtrationthe product is collected by filtration
  6. customRecrystallization from chloroform, acetone, isopropanol
  7. customyields the product of this example as a colorless solid

出典と根拠

ORDレコード
ord-bfca8a80961545bfb086bb09b118e29e
出典データセット
uspto-grants-1985_11
特許番号
US04551463

反応ノート

読み込み中…