Sodium Hydroxide → (2E)-3-(6-aminopyridin-3-yl)prop-2-enoic acid

HRID 1710485Notes

Reaction equation

HRID 1710485 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]([O:12]CC2C=CC=CC=2)=[O:11])=[CH:4][CH:3]=1.[OH-].[Na+]>CO>[NH2:1][C:2]1[N:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]([OH:12])=[O:11])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 11128853benzyl (E)-3-(6-aminopyridin-3-yl)acrylate

Product 1

HCID 10487224(2E)-3-(6-aminopyridin-3-yl)prop-2-enoic acidYield 72%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of benzyl (E)-3-(6-aminopyridin-3-yl)acrylate (1.3 g, 5.1 mmole) and 1.0 N NaOH (10 mL, 10 mmole) in MeOH was heated at reflux overnight. The solution was concentrated in vacuo, and the residue was dissolved in H2O. The pH was adjusted to 6 with dilute HCl, and the solid precipitate was collected by suction filtration and dried to give the title compound (0.6 g, 72%) as a white solid: MS (ES) m/e 165 (M+H)+.

Workup

  1. temperatureat reflux overnight
  2. concentrationThe solution was concentrated in vacuo
  3. dissolutionthe residue was dissolved in H2O
  4. filtrationthe solid precipitate was collected by suction filtration
  5. customdried

Sources & evidence

ORD record
ord-4707c9e4bc094de5b98ab3e2153a9271
Source dataset
uspto-grants-2010_09
Patent number
US07790716B2

Reaction notes

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