Methanol → HCID 178498304, compound

HRID 249481Notes

Reaction equation

HRID 249481 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][N:3]=1.OS(O)(=O)=O.[CH3:16]O>>[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH3:16])=[O:7])=[CH:4][N:3]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 178418479HCID 178418479, compound

Product 1

HCID 178498304HCID 178498304, compound

Procedure

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.

Workup

  1. temperatureThe mixture was refluxed for 10 hours
  2. temperatureAfter cooling
  3. distillationMeOH was distilled off
  4. filtrationThe precipitate was collected by filtration
  5. washrinsed (twice) with water
  6. customdried

Sources & evidence

ORD record
ord-ad158c40df6844a698df8f3c21dcfb77
Source dataset
uspto-grants-1993_05
Patent number
US05214152

Reaction notes

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