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

HRID 867393Notes

Reaction equation

HRID 867393 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 gamma-butyrolactone there was added, under nitrogen, 13.4 g. of potassium tertiary butoxide. The reaction mixture was heated and stirred for one hour at 95° C., poured on ice and stirred overnight. The mixture was extracted with ether, the aqueous layer acidified with acetic acid to pH 4.5 and the product was collected by filtration. Recrystallization from chloroform, acetone, isopropanol yielded the product of this example as a colorless solid; m.p. 235°-236° C.

Workup

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

Sources & evidence

ORD record
ord-9272ad5f7ba64ed8b92b20ecc00a3b8d
Source dataset
uspto-grants-1988_10
Patent number
US04775524

Reaction notes

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