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

HRID 1906173Notes

Reaction equation

HRID 1906173 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-09a7ce122d8b48e8bb367ad01fabac32
Source dataset
uspto-grants-1987_03
Patent number
US04650793

Reaction notes

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