Methanol → HCID 178498304, compound

HRID 1585002Notes

Reaction equation

HRID 1585002 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-496e3909db044d4a916cd50f407bed8e
Source dataset
uspto-grants-1999_08
Patent number
US05935981

Reaction notes

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