Ethanol → Ethyl 3-Aminoisonicotinate

HRID 227584

Reaction equation

HRID 227584 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[C:8]([OH:10])=[O:9].S(=O)(=O)(O)O.[NH4+].[OH-].[CH2:18](O)[CH3:19]>>[NH2:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[C:8]([O:10][CH2:18][CH3:19])=[O:9]

Participants

5

Reactant 4

HCID 702EthanolHCID 1118Sulfuric AcidHCID 14923Ammonium HydroxideHCID 4595313-Aminoisonicotinic acid

Product 1

HCID 2736365Ethyl 3-AminoisonicotinateYield 87%

Procedure

To a solution of 1 g (7.25 mmol) of 3-amino-4-pyridinecarboxylic acid in 5 mL of ethyl alcohol was added 2 mL of sulfuric acid. The mixture was warmed under reflux for 2 h. It was cooled and basified with conc. NH4OH solution to pH=8. The resulting solution was extracted with ethyl acetate and the organic layer was washed with brine and water, dried (MgSO4) and concentrated in vacuo to give 1.04 g of the title compound as a white solid (87%).

Workup

  1. temperatureThe mixture was warmed
  2. temperatureunder reflux for 2 h
  3. temperatureIt was cooled
  4. extractionThe resulting solution was extracted with ethyl acetate
  5. washthe organic layer was washed with brine and water
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-67d96eb2975649e3885db6bf1f096cfe
Source dataset
uspto-grants-2009_07
Patent number
US07560564B2

Linked notes

Loading…