1-Tert-butyl 3-ethyl 2-(6-nitropyridin-3-yl)malonate → Ethyl 2-(6-nitropyridin-3-yl)acetate

HRID 2173311Notes

Reaction equation

HRID 2173311 reaction equation
[N+:1]([C:4]1[N:9]=[CH:8][C:7]([CH:10](C(OCC)=O)[C:11]([O:13][C:14](C)(C)[CH3:15])=[O:12])=[CH:6][CH:5]=1)([O-:3])=[O:2]>C(O)(C(F)(F)F)=O.C(Cl)Cl>[N+:1]([C:4]1[N:9]=[CH:8][C:7]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

3

Reactant 1

HCID 673939371-Tert-butyl 3-ethyl 2-(6-nitropyridin-3-yl)malonate

Product 1

HCID 21300451Ethyl 2-(6-nitropyridin-3-yl)acetate

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

A mixture of tert-butyl ethyl (6-nitropyridin-3-yl)propanedioate (1.4 g, 4.5 mmol) in a mixed solution of TFA/DCM (10 mL/10 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 (6-nitropyridin-3-yl)acetate. 1H-NMR (400 MHz, CDCl3) δ 8.57 (s, 1H), 8.27 (d, J=8.4 Hz, 1H), 8.03 (dd, J=2.4 Hz, 8.4 Hz, 1H), 4.22 (q, J=7.2 Hz, 2H), 3.81 (s, 2H), 1.30 (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-ef1b3569fe3340988f3a2321f86bf2f1
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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