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

HRID 355277Notes

Reaction equation

HRID 355277 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 (5 g) is suspended in ethylbromoacetate (20 ml) and the mixture 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 (5.4 g), m.p. 141°-151° C.; νmax (nujol) 1645, 1720 cm-1 ; δ(d6DMSO), 1.0 (t, 3H), 4.0 (q, 2H), 4.55 (s, 2H), 5.95 (t, 1H), 6.6(d, 1H), 7.05 (d, 1H).

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-399d56dcb9a74510b96214ab279a26a3
Source dataset
uspto-grants-1998_11
Patent number
USRE035948

Reaction notes

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