Methanol → Methyl 6-amino-2-methylpyridine-3-carboxylate

HRID 2411164Notes

Reaction equation

HRID 2411164 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([CH3:11])[N:3]=1.S(=O)(=O)(O)O.[OH-].[Na+].[CH3:19]O>>[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH3:19])=[O:7])=[C:4]([CH3:11])[N:3]=1

Participants

5

Reactant 4

HCID 887MethanolHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 288755296-Amino-2-methylpyridine-3-carboxylic acid

Product 1

HCID 55252884Methyl 6-amino-2-methylpyridine-3-carboxylate

Procedure

6-Amino-2-methylnicotinic acid (1.00 g) was suspended in methanol (15 mL), concentrated sulfuric acid (0.5 mL) was added, and the mixture was stirred with heating under reflux for 18 hr. The reaction mixture was cooled, aqueous sodium hydroxide solution was added, and the mixture was extracted with chloroform. The organic layer was washed with saturated brine, and the solvent was evaporated to give the title compound (0.82 g).

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for 18 hr
  3. temperatureThe reaction mixture was cooled
  4. extractionthe mixture was extracted with chloroform
  5. washThe organic layer was washed with saturated brine
  6. customthe solvent was evaporated

Sources & evidence

ORD record
ord-0abe182b5c4c4cc68431c8cbc27e4d99
Source dataset
uspto-grants-2014_08
Patent number
US08816079B2

Reaction notes

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