Methanol → Methyl 6-aminonicotinate

HRID 2272822Notes

Reaction equation

HRID 2272822 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]([OH:10])=[O:9])=[CH:4][CH:3]=1.OS(O)(=O)=O.[CH3:16]O>>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]([O:10][CH3:16])=[O:9])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 184966-Aminonicotinic acid

Product 1

HCID 737487Methyl 6-aminonicotinateYield 72%

Conditions

Temperature
80 °C

Procedure

To a solution of 6-aminopyridine 3-carboxylic acid (30 g, 217.1 mmol) in methanol (30 mL) is added H2SO4 (30 mL at 0° C.) and the reaction mixture is heated to 80° C. for 16 hours. The reaction mixture is evaporated and the residue is neutralized with aqueous NaHCO3 solution (50 mL), the precipitated solid is filtered and dried to give the title compound as a pale yellow solid (24 g, 72%). LCMS m/z 153(M+H)+.

Workup

  1. customThe reaction mixture is evaporated
  2. filtrationthe precipitated solid is filtered
  3. customdried

Sources & evidence

ORD record
ord-15aa84ae3bb14276a559757e8d2ccec8
Source dataset
uspto-grants-2015_09
Patent number
US09120793B2

Reaction notes

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