Ethyl 3-oxo-3-(pyridin-2-yl)propanoate → HCID 178472895, compound

HRID 714928

Reaction equation

HRID 714928 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[O:8].[N:15]([O-])=[O:16].[Na+]>C(O)(=O)C.O>[OH:16][N:15]=[C:9]([C:7](=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=1)[C:10]([O:12][CH2:13][CH3:14])=[O:11]

Participants

5

Reactant 2

HCID 2736461Ethyl 3-oxo-3-(pyridin-2-yl)propanoateHCID 23668193Sodium Nitrite

Product 1

HCID 178472895HCID 178472895, compoundYield 61.5%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Procedure

To a stirred solution of ethyl picolinoylacetate (0.500 g, 2.6 mmol) in acetic acid (0.5 mL) was added a solution of sodium nitrite (0.238 g, 3.4 mmol) in water (0.5 mL), dropwise. The resulting solution was stirred at room temperature for 2 hours after which water (0.5 mL) was added and the reaction was stirred for a further 2 hours. The mixture was extracted with Et2O and the combined organic phase was washed with water, saturated sodium bicarbonate solution and brine, dried over MgSO4 and the solvent removed in vacuo to afford ethyl 2-(hydroxyimino)-3-oxo-3-(pyridin-2-yl)propanoate (0.353 g, 1.6 mmol, 61%) as a white solid. 1H NMR (DMSO) δ 1.17 (3H, t), 4.22 (2H, q), 7.74 (1H, m), 8.04-8.11 (2H, m), 8.74 (1H, m), 12.87 (1H, s). LCMS (2) Rt: 1.09 min; m/z (ES+) 223.

Workup

  1. additionwas added
  2. extractionThe mixture was extracted with Et2O
  3. washthe combined organic phase was washed with water, saturated sodium bicarbonate solution and brine
  4. dry with materialdried over MgSO4
  5. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-4540f02f705b4cc6b8531fc74e77a5ee
Source dataset
uspto-grants-2015_11
Patent number
US09187465B2

Linked notes

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