Carbon Dioxide → ethyl 2-(3-hydroxy-2-oxopyridin-1(2H)-yl)acetate

HRID 1030072Notes

Reaction equation

HRID 1030072 reaction equation
[OH:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][N:3]=1.C(=O)=O.[CH2:12]([O:14][C:15](=[O:18])[CH2:16]Br)[CH3:13]>>[CH2:12]([O:14][C:15]([CH2:16][N:3]1[CH:4]=[CH:5][CH:6]=[C:7]([OH:8])[C:2]1=[O:1])=[O:18])[CH3:13]

Participants

4

Reactant 3

HCID 280Carbon DioxideHCID 7748Ethyl bromoacetateHCID 178516237HCID 178516237, compound

Product 1

HCID 11127212ethyl 2-(3-hydroxy-2-oxopyridin-1(2H)-yl)acetate

Conditions

Temperature
140 °C

Procedure

2,3-Dihydroxypyridine (10 g) is suspended in ethylbromoacetate (40 ml) and the mixture is heated in a sealed tube for 24 hours at 140° C. The tube is then cooled in solid CO2 and opened. The contents are subjected to rotary evaporation at 50° C. to yield a yellow solid. Recrystallisation of this solid from water yields 1-ethoxycarbonylmethyl-3-hydroxypyrid-2-one as white crystals (10.8 g), m.p. 141°-151° C.

Workup

  1. customThe contents are subjected to rotary evaporation at 50° C.
  2. customto yield a yellow solid
  3. customRecrystallisation of this solid from water

Sources & evidence

ORD record
ord-6bfc8c0dab0b49478e1607a497839094
Source dataset
uspto-grants-1992_04
Patent number
US05104865

Reaction notes

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