Reaktion #336663

ord-ad158c40df6844a698df8f3c21dcfb77

Reaktionsgleichung

O=C(O)c1ccc(O)nc1
6-hydroxynicotinic acid
O=S(=O)(O)O
H2SO4
CO
MeOH
COC(=O)c1ccc(O)nc1
methyl 6-hydroxynicotinate

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    TemperaturThe mixture was refluxed for 10 hours
  2. 2
    TemperaturAfter cooling
  3. 3
    workup.DISTILLATIONMeOH was distilled off
  4. 4
    FiltrationThe precipitate was collected by filtration
  5. 5
    Waschenrinsed (twice) with water
  6. 6
    Sonstigedried

Vorschrift

In 70 ml of MeOH was suspended 12.0 g (0.086 mole) of 6-hydroxynicotinic acid followed by addition of 4 ml of concentrated H2SO4. The mixture was refluxed for 10 hours. After cooling, MeOH was distilled off and the residue was adjusted to pH about 8 with a saturated aqueous solution of sodium hydrogen carbonate. The precipitate was collected by filtration, rinsed (twice) with water and dried to give 10.5 g of methyl 6-hydroxynicotinate as pale yellow crystals. This product was in the pyridone structure.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05214152uspto-grants-1993_05