Hydrochloric Acid → 2-(5-Nitro-3-(trifluoromethyl)pyridin-2-yl)acetonitrile

HRID 576159Notes

Reaction equation

HRID 576159 reaction equation
[C:1]([CH:3]([C:11]1[C:16]([C:17]([F:20])([F:19])[F:18])=[CH:15][C:14]([N+:21]([O-:23])=[O:22])=[CH:13][N:12]=1)C(OC(C)(C)C)=O)#[N:2].Cl>CO>[N+:21]([C:14]1[CH:15]=[C:16]([C:17]([F:20])([F:18])[F:19])[C:11]([CH2:3][C:1]#[N:2])=[N:12][CH:13]=1)([O-:23])=[O:22]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 90416649Tert-butyl 2-cyano-2-(5-nitro-3-(trifluoromethyl)pyridin-2-yl)acetate

Product 1

HCID 904161702-(5-Nitro-3-(trifluoromethyl)pyridin-2-yl)acetonitrileYield 54.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of tert-butyl 2-cyano-2-(5-nitro-3-(trifluoromethyl)pyridin-2-yl)acetate (1.06 g, 3.20 mmol) in MeOH (80 mL) was added HCl (20 mL, 3.20 mmol). The mixture was at 70° C. for 10 h. Then the solution was concentrated and distributed between EA and saturated NaHCO3 solution. The combined organic extract was washed with brine, dried over MgSO4, filtered and concentrated. The resulting 2-(5-nitro-3-(trifluoromethyl)pyridin-2-yl)acetonitrile (402 mg, 1.739 mmol, 54.4% yield) was used in the next step without further purification. TLC (PE/EA=5:1, Rf=0.6): 1H NMR (400 MHz, CDCl3) δ 9.56 (d, J=2.21 Hz, 1H), 8.63-8.87 (m, 1H), 4.20 (br. s., 2H); ES-LCMS m/z 232.0 (M+H).

Workup

  1. concentrationThen the solution was concentrated
  2. extractionThe combined organic extract
  3. washwas washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-1a36094861e2451abadeee6820f31cc7
Source dataset
uspto-grants-2015_05
Patent number
US09035063B2

Reaction notes

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