Ammonia → Methyl 5-hydroxypyridine-3-carboxylate

HRID 2264155Notes

Reaction equation

HRID 2264155 reaction equation
[OH:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].N.[CH3:12]O>>[OH:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7]([O:9][CH3:12])=[O:8]

Participants

4

Reactant 3

HCID 222AmmoniaHCID 887Methanol2×HCID 340375-Hydroxynicotinic acid

Product 1

HCID 354317Methyl 5-hydroxypyridine-3-carboxylate

Procedure

A mixture of 1 g of 5-hydroxynicotinic acid, 2 g Amberlyst 15 ion-exchange resin and 150 mL of methanol was heated to reflux with stirring for 24 hrs, cooled, basified with 10% ammonia in methanol, filtered and concentrated under reduced pressure. The residue was taken up in 50 mL of chloroform and dried over MgSO4. Concentration under reduced pressure gave a tan crystalline solid: MS (m+1)=154.1; 1H NMR (400 MHz, CDCl3) 8.68 (s, 1H), 8.32 (s, 1H), 7.72 (s, 1H), 3.94 (s, 3H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux
  3. temperaturecooled
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. dry with materialdried over MgSO4
  7. concentrationConcentration under reduced pressure
  8. customgave a tan crystalline solid

Sources & evidence

ORD record
ord-f76c5682dc3541a88ff78e3382478e95
Source dataset
uspto-grants-2010_12
Patent number
US07855201B2

Reaction notes

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