Formic Acid → 3-Hydroxy-2-oxo-1(2H)-pyridineacetic acid

HRID 1871787Notes

Reaction equation

HRID 1871787 reaction equation
C([O:3][C:4]([CH2:6][N:7]1[CH:12]=[CH:11][CH:10]=[C:9]([OH:13])[C:8]1=[O:14])=[O:5])C.C(O)=O>C(O)C.O>[C:4]([CH2:6][N:7]1[CH:12]=[CH:11][CH:10]=[C:9]([OH:13])[C:8]1=[O:14])([OH:5])=[O:3]

Participants

4

Reactant 2

HCID 284Formic AcidHCID 11127212ethyl 2-(3-hydroxy-2-oxopyridin-1(2H)-yl)acetate

Product 1

HCID 100123083-Hydroxy-2-oxo-1(2H)-pyridineacetic acidYield 81.6%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Conditions

Temperature
60 °C

Procedure

1-Ethoxycarbonylmethyl-3-hydroxypyrid-2-one (2 g) is dissolved in 15 ml of 1:2 v/v ethanol/water containing sufficient ammonium hydroxide to create a pH of 12.0. The solution is heated at 60° C. for 30 minutes, cooled, and acidified to pH 3.0 by the addition of formic acid. The solution is rotary evaporated to remove most of the ethanol and then freeze dried for 20 hours to remove the water, formic acid and ammonium formate. The resulting solid is recrystallised from water to yield white crystals (1.4 g), m.p. 203°-205° C.; νmax (nujol) 1540, 1590, 1640, 1695, 3240 cm-1 ; δ(d6DMSO) 4.5 (s, 2H), 5.95 (t, 1H), 6.6 (d, 1H), 7.0 (d, 1H).

Workup

  1. temperaturecooled
  2. customThe solution is rotary evaporated
  3. customto remove most of the ethanol
  4. customfreeze dried for 20 hours
  5. customto remove the water, formic acid and ammonium formate
  6. customThe resulting solid is recrystallised from water

Sources & evidence

ORD record
ord-002c8b98d40c4f0da5a4126074c24de0
Source dataset
uspto-grants-2000_08
Patent number
USRE036831

Reaction notes

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