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

HRID 1502107Notes

Reaction equation

HRID 1502107 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 title compound. 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-210190040cf24f68a7e67045266c73cc
Source dataset
uspto-grants-2015_12
Patent number
US09206199B2

Reaction notes

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