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

HRID 1825925Notes

Reaction equation

HRID 1825925 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-73dcc04af534439c96018f30cf367113
Source dataset
uspto-grants-2006_05
Patent number
US07049310B2

Reaction notes

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