Ethanamine, 2,2,2-trifluoro- → 2-Pyridinamine, 5-nitro-N-(2,2,2-trifluoroethyl)-

HRID 2236167Notes

Reaction equation

Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.[F:11][C:12]([F:16])([F:15])[CH2:13][NH2:14].C(N(CC)C(C)C)(C)C>CN1CCCC1=O>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([NH:14][CH2:13][C:12]([F:16])([F:15])[F:11])=[N:3][CH:4]=1)([O-:10])=[O:9]

Participants

Conditions

Temperature: 200 °C

Procedure

A mixture of 2-chloro-5-nitro-pyridine (500 mg, 3.15 mmol), 2,2,2-trifluoro-ethylamine (940 mg, 9.45 mmol) and N,N-diisopropylethylamine (1.64 mL, 9.45 mmol) in 1-methyl-pyrrolidin-2-one (10 mL) in a sealed tube was heated by microwave at 200° C. for 10 minutes. The reaction mixture was evaporated to dryness and purified by silica gel chromatography (Isco 120 g column, 40% ethyl acetate/hexanes) to give (5-nitro-pyridin-2-yl)-(2,2,2-trifluoro-ethyl)-amine (300 mg, 43%) as a yellow solid. LCMS calcd for C7H6F3N3O2 (m/e) 221, obsd 222 (M+H). The NMR spectrum obtained on the sample is compatible with its structure.

Workup

customThe reaction mixture was evaporated to dryness
custompurified by silica gel chromatography (Isco 120 g column, 40% ethyl acetate/hexanes)

Sources & evidence

ORD record: ord-bdf61da713a5414faa9d477edd221c8c
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07714126B2

Reaction notes

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