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

HRID 1432895Notes

Reaction equation

HRID 1432895 reaction equation
C([NH:4][C:5]1[N:10]=[CH:9][C:8]([CH:11]=[CH:12][C:13]([OH:15])=[O:14])=[CH:7][CH:6]=1)(=O)C.[OH-].[Na+]>C(O)C>[NH2:4][C:5]1[N:10]=[CH:9][C:8]([CH:11]=[CH:12][C:13]([OH:15])=[O:14])=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 54024436HCID 54024436, compound

Product 1

HCID 534008323-(6-Aminopyridin-3-yl)prop-2-enoic acidYield 49.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 3-(6-acetylamino-pyridin-3-yl)-acrylic acid (0.80 g, 3.88 mmol) in ethanol (10 mL) is added 1N NaOH (20 mL). The solution is heated to reflux. After 16 h, the solution is concentrated to ⅓ its volume. The aqueous solution is diluted with water and acidified to pH=2 with 6N HCl. The solution is concentrated to dryness. The residue is dissolved in methanol. The solution is filtered. The organic solution is concentrated. The crude product is purified by RP-HPLC eluting with a gradient of 5%CH3CN/H2O (0.1% TFA) to 30% CH3CN/H2O (0.1%TFA) to give the product as a white solid (0.54 g, 1.93 mmol). 1H NMR (300 MHz, CD3OD) δ8.34 (d, 1H), 8.07 (s, 1H), 7.54 (d, 2H), 7.06 (d, 1H), 6.47 (d, 1H). MS (ion spray) 165, (M+H).

Workup

  1. temperatureThe solution is heated to reflux
  2. concentrationthe solution is concentrated
  3. additionThe aqueous solution is diluted with water
  4. concentrationThe solution is concentrated to dryness
  5. dissolutionThe residue is dissolved in methanol
  6. filtrationThe solution is filtered
  7. concentrationThe organic solution is concentrated
  8. customThe crude product is purified by RP-HPLC
  9. washeluting with a gradient of 5%CH3CN/H2O (0.1% TFA) to 30% CH3CN/H2O (0.1%TFA)

Sources & evidence

ORD record
ord-6e42566a9fc7407fa91d74b9364aad46
Source dataset
uspto-grants-2009_11
Patent number
US07612075B2

Reaction notes

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