Ethanol → Ethyl 6-Aminonicotinate

HRID 85153

Reaction equation

HRID 85153 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([OH:10])=[O:9])=[CH:4][N:3]=1.O=S(Cl)Cl.[CH2:15](O)[CH3:16]>>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([O:10][CH2:15][CH3:16])=[O:9])=[CH:4][N:3]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 184966-Aminonicotinic acidHCID 24386Thionyl Chloride

Product 1

HCID 235927Ethyl 6-AminonicotinateYield 94%

Procedure

To a solution of 2-amino-5-pyridinecarboxylic acid (98; 5.0 g, 36.2 mmol) in ethanol (100 mL) was added SOCl2 (8.6 g, 72.4 mmol) at 0° C. The resulting reaction mixture was stirred under reflux for 12 h. Upon cooling to room temperature, the reaction mixture was concentrated under reduced pressure and then enough saturated aqueous Na2CO3 solution was added to the reaction mixture to adjust the pH=9. The resulting solids were collected by filtration and dried to afford ethyl 6-aminonicotinate 99 (5.64 g, 94%).

Workup

  1. customThe resulting reaction mixture
  2. temperatureunder reflux for 12 h
  3. concentrationthe reaction mixture was concentrated under reduced pressure
  4. additionenough saturated aqueous Na2CO3 solution was added to the reaction mixture
  5. filtrationThe resulting solids were collected by filtration
  6. customdried

Sources & evidence

ORD record
ord-3b5ab5f465944b598aefea8249ab03d3
Source dataset
uspto-grants-2014_09
Patent number
US08846947B2

Linked notes

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