Sodium Hydroxide → 5-Amino-6-methylpyridine-3-carboxylic acid

HRID 541421Notes

Reaction equation

HRID 541421 reaction equation
[NH2:1][C:2]1[C:3]([CH3:12])=[N:4][CH:5]=[C:6]([CH:11]=1)[C:7]([O:9]C)=[O:8].[OH-].[Na+]>CO.O>[NH2:1][C:2]1[C:3]([CH3:12])=[N:4][CH:5]=[C:6]([CH:11]=1)[C:7]([OH:9])=[O:8]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58662456Methyl 5-amino-6-methylnicotinate

Product 1

HCID 220063995-Amino-6-methylpyridine-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

Into a round-bottom flask, was placed a solution of methyl 5-amino-6-methylnicotinate (5.00 g, 30.1 mmol, 1.00 equiv) and sodium hydroxide (20 g) in MeOH/H2O (80/200 mL). The resulting solution was heated at reflux overnight. After cooling to ambient temperature, the methanol was removed under reduced pressure. The pH of the remaining aqueous phase was adjusted to 4 with aqueous hydrogen chloride (2 M). The resulting mixture was then concentrated under reduced pressure to yield 5.00 g (crude) of the title compound as a yellow solid.

Workup

  1. customInto a round-bottom flask, was placed
  2. temperatureThe resulting solution was heated
  3. temperatureat reflux overnight
  4. customthe methanol was removed under reduced pressure
  5. concentrationThe resulting mixture was then concentrated under reduced pressure

Sources & evidence

ORD record
ord-7603258d28de4638b87ea6ef9c00fe26
Source dataset
uspto-grants-2014_10
Patent number
US08871790B2

Reaction notes

Loading…