HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → 2-(5-Nitro-3-(trifluoromethyl)pyridin-2-yl)acetonitrile
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Tert-butyl 2-cyano-2-(5-nitro-3-(trifluoromethyl)pyridin-2-yl)acetate | HCID 90416649 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | 2-(5-Nitro-3-(trifluoromethyl)pyridin-2-yl)acetonitrile | HCID 90416170 | 54.4% |
Reaction Steps
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).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09035063B2 |
| Source dataset | uspto-grants-2015_05 |
| ORD ID | ord-1a36094861e2451abadeee6820f31cc7 |
| Source note | uspto-grants-2015_05 |