Trifluoroacetic acid → Ethyl 2-(5-nitropyridin-2-YL)acetate

HRID 602443Notes

Reaction equation

HRID 602443 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH:10](C(OCC)=O)[C:11]([O:13][C:14](C)(C)[CH3:15])=[O:12])=[N:8][CH:9]=1)([O-:3])=[O:2].FC(F)(F)C(O)=O>ClCCl>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[N:8][CH:9]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 54383765tert-Butyl ethyl (5-nitropyridin-2-yl)malonate

Product 1

HCID 18670679Ethyl 2-(5-nitropyridin-2-YL)acetateYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of tert-butyl ethyl (5-nitropyridin-2-yl)malonate (6.93 g, 22.3 mmol, step 1 of Example 1) in dichloromethane (75 mL) was added trifluoroacetic acid (7.64 g, 67.0 mmol) at room temperature, and the mixture was stirred at room temperature for 20 h. The mixture was washed with saturated aqueous sodium hydrogencarbonate solution, dried over magnesium sulfate and concentrated under reduced pressure. The resulting residue was chromatographed on a column of silica gel eluting with n-hexane/ethyl acetate (5:1 to 4:1) to give 3.27 g (70%) of the title compound as an orange oil.

Workup

  1. washThe mixture was washed with saturated aqueous sodium hydrogencarbonate solution
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue was chromatographed on a column of silica gel eluting with n-hexane/ethyl acetate (5:1 to 4:1)

Sources & evidence

ORD record
ord-866c13c1b79d43e0a2302250bdb14355
Source dataset
uspto-grants-2011_03
Patent number
US07906532B2

Reaction notes

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