Ethanol → Ethyl 3-Aminoisonicotinate

HRID 868957

Reaction equation

HRID 868957 reaction equation
[NH2:1][C:2]1[CH:10]=[N:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].S(=O)(=O)(O)O.[CH2:16](O)[CH3:17]>C1(C)C=CC=CC=1>[NH2:1][C:2]1[CH:10]=[N:9][CH:8]=[CH:7][C:3]=1[C:4]([O:6][CH2:16][CH3:17])=[O:5]

Participants

5

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 4595313-Aminoisonicotinic acid

Product 1

HCID 2736365Ethyl 3-Aminoisonicotinate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To an ice-cold suspension of 3-aminoisonicotinic acid (8 g, 58 mmol) in ethanol (36 mL) and toluene (36 mL) was added concentrated sulfuric acid (6.4 mL), and the mixture was stirred for 24 h. The solvents were removed under reduced pressure, the residue was dissolved in water, and the solution was adjusted to pH 8 with concentrated ammonium hydroxide to give ethyl 3-aminoisonicotinate (6.5 g). MS (ESI): m/z 167 [M+H]+.

Workup

  1. customThe solvents were removed under reduced pressure
  2. dissolutionthe residue was dissolved in water

Sources & evidence

ORD record
ord-5af5714a24524f9b806dd5e0a82c303d
Source dataset
uspto-grants-2015_03
Patent number
US08969349B2

Linked notes

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