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

HRID 1050128Notes

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.CC(=O)OCC>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

Conditions

Temperature: 100 °C

Procedure

To a solution of tert-butyl 2-cyano-2-(5-nitro-3-(trifluoromethyl)pyridin-2-yl)acetate (7 g, 21.13 mmol) in MeOH (100 mL) was added aqueous HCl (40 mL, 1316 mmol). The resulting mixture was stirred at 100° C. overnight. After TLC analysis (PE/EA=10/1) showed the starting material was consumed, the solvent was removed in vacuo. The residue was dissolved in H2O (50 mL) and extracted by EA (100 mL). The organic layer was washed with aqueous NaHCO3 and brine and then dried over Na2SO4. After filtration, the filtrate was concentrated to give the crude product, which was purified by column chromatography (PE/EA=10/1) to yield a brown solid of 2-(5-nitro-3-(trifluoromethyl)pyridin-2-yl)acetonitrile (4.3 g, 17.77 mmol, 84% yield): 1H NMR (400 MHz, CD3OD) δ 9.59 (s, 1H), 8.88 (d, J=2.4 Hz, 1H), 4.86 (s, 2H); ES-LCMS m/z: 232.1 (M+H).

Workup

customwas consumed
customthe solvent was removed in vacuo
dissolutionThe residue was dissolved in H2O (50 mL)
extractionextracted by EA (100 mL)
washThe organic layer was washed with aqueous NaHCO3 and brine
dry with materialdried over Na2SO4
filtrationAfter filtration
concentrationthe filtrate was concentrated
customto give the crude product, which
customwas purified by column chromatography (PE/EA=10/1)

Sources & evidence

ORD record: ord-518ed1bcacad4c898cfac019ff1e9bf1
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09382238B2

Reaction notes

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