Ethanol → Ethyl 6-Aminonicotinate

HRID 520494Notes

Reaction equation

HRID 520494 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([OH:10])=[O:9])=[CH:4][N:3]=1.S(Cl)(Cl)=O.[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 88%

Procedure

To a solution of 2-amino-5-pyridinecarboxylic acid 113 (150 g, 1.09 mol) in ethanol (2 L) was added thionyl chloride (259 g, 2.18 mol) at 0° C. The mixture was heated at reflux for 12 h. The solvent was removed under reduced pressure. Saturated aq Na2CO3 was added to adjust the pH to 9 and the resulting solid was collected by filtration, rinsed with H2O, and dried to give 114 (160 g, 88% yield).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 12 h
  3. customThe solvent was removed under reduced pressure
  4. additionSaturated aq Na2CO3 was added
  5. filtrationthe resulting solid was collected by filtration
  6. washrinsed with H2O
  7. customdried

Sources & evidence

ORD record
ord-ffff6b5e86ea40c6a5e886111b1a5083
Source dataset
uspto-grants-2016_05
Patent number
US09326986B2

Reaction notes

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