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

HRID 1583314Notes

Reaction equation

HRID 1583314 reaction equation
[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

Participants

4

Reactant 3

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

Product 1

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

Conditions

Temperature
95 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-bfca8a80961545bfb086bb09b118e29e
Source dataset
uspto-grants-1985_11
Patent number
US04551463

Reaction notes

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