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

HRID 1920964Notes

Reaction equation

HRID 1920964 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-37f56f0ef54e4dab8539a6477115f6e9
Source dataset
uspto-grants-2012_05
Patent number
US08173646B2

Reaction notes

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