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

HRID 1583314노트

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HRID 1583314 반응식
[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

참가 물질

4

반응물 3

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

생성물 1

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

반응 조건

온도
95 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-bfca8a80961545bfb086bb09b118e29e
출처 데이터셋
uspto-grants-1985_11
특허 번호
US04551463

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