Ethylamine → Ethyl-(5-nitro-2-trifluoromethyl-pyridin-4-yl)-amine

HRID 1988749Notes

Reaction equation

HRID 1988749 reaction equation
C([O-])([O-])=O.[K+].[K+].[CH2:7]([NH2:9])[CH3:8].Cl[C:11]1[C:16]([N+:17]([O-:19])=[O:18])=[CH:15][N:14]=[C:13]([C:20]([F:23])([F:22])[F:21])[CH:12]=1>C1COCC1.C(#N)C>[CH2:7]([NH:9][C:11]1[C:16]([N+:17]([O-:19])=[O:18])=[CH:15][N:14]=[C:13]([C:20]([F:23])([F:21])[F:22])[CH:12]=1)[CH3:8]

Participants

6

Reactant 3

HCID 6341EthylamineHCID 11430Potassium CarbonateHCID 223800514-Chloro-5-nitro-2-(trifluoromethyl)pyridine

Product 1

HCID 22380174Ethyl-(5-nitro-2-trifluoromethyl-pyridin-4-yl)-amine

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

K2CO3 (4.15 g, 30.01 mmol), and 2.0 M solution of EtNH2 (15 mL, 30.01 mmol) in THF are added to a solution of 4-chloro-5-nitro-2-trifluoromethyl-pyridine (3.4 g, 15.0 mmol) in acetonitrile (30 mL) under cold conditions. The reaction is complete after stirring at 0° C. for 2 h. Usual work up affords ethyl-(5-nitro-2-trifluoromethyl-pyridin-4-yl)-amine as an yellow-orange viscous oil. 1H NMR (300 MHz, CDCl3) δ 9.24 (s, 1H) 7.09 (s, 1H), 3.45 (t, J=7.2 Hz, 2H), 1.42 (t, J=7.2 Hz, 3H).

Sources & evidence

ORD record
ord-564c3c34f64f437586f8ad889f93d388
Source dataset
uspto-grants-2010_01
Patent number
US07642267B2

Reaction notes

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