Ethyl 2-pyridylacetate → Nsc74475

HRID 23961Notes

Reaction equation

HRID 23961 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9].[N:13]([O-])=[O:14].[Na+]>C(O)(=O)C.O>[OH:14][N:13]=[C:7]([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=1)[C:8]([O:10][CH2:11][CH3:12])=[O:9]

Participants

5

Reactant 2

HCID 75960Ethyl 2-pyridylacetateHCID 23668193Sodium Nitrite

Product 1

HCID 135543845Nsc74475Yield 95.2%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Procedure

To a stirring solution of ethyl pyridine-2-acetate (12.6 g, 76.3 mmol) in acetic acid (19 mL) at 5° C. was added a solution of sodium nitrite (6.05 g, 87.7 mmol) in water (12 mL) at a rate sufficient to maintain the internal temperature below 15° C. After complete addition and an additional 30 min, an additional 30 mL of water was added. The resulting white precipitate was filtered, washed with water, saturated aqueous NaHCO3, and again with water. The solid was then dried under vacuum to give 14.1 g (95%) of the title compound.

Workup

  1. temperatureto maintain the internal temperature below 15° C
  2. additionAfter complete addition
  3. filtrationThe resulting white precipitate was filtered
  4. washwashed with water, saturated aqueous NaHCO3
  5. customThe solid was then dried under vacuum

Sources & evidence

ORD record
ord-a7f6fb272a334a2483dacd0a71bbf705
Source dataset
uspto-grants-2005_02
Patent number
US06855715B1

Reaction notes

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