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

HRID 2173322Notes

Reaction equation

HRID 2173322 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].C(O)(C(F)(F)F)=O.C(Cl)Cl>>[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

3

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 54383765tert-Butyl ethyl (5-nitropyridin-2-yl)malonate

Product 1

HCID 18670679Ethyl 2-(5-nitropyridin-2-YL)acetate

Procedure

A mixture of tert-butyl ethyl (5-nitropyridin-2-yl)propanedioate (4.10 g, 13.2 mmol) in a mixed solution of TFA/DCM (4 mL/20 mL) was stirred for 5 hours at room temperature. The mixture was concentrated under reduce pressure. The residue was dissolved with DCM, washed with sat. NaHCO3, dried over anhydrous Na2SO4 and concentrated to give ethyl (5-nitropyridin-2-yl)acetate. 1H-NMR (400 MHz, CDCl3) δ 9.41 (s, 1H), 8.58 (d, J=8.4 Hz, 1H), 7.64 (d, J=8.4 Hz, 1H), 4.16 (q, J=7.2 Hz, 2H), 4.02 (s, 2H), 1.22 (t, J=7.2 Hz, 3H).

Workup

  1. concentrationThe mixture was concentrated
  2. dissolutionThe residue was dissolved with DCM
  3. washwashed with sat. NaHCO3
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-2169cf657b014fb59f06011b9d249782
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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