Ethanol → 5-Ethoxy-2-nitroaniline
Reaction equation
[Na].Cl[C:3]1[CH:4]=[CH:5][C:6]([N+:10]([O-:12])=[O:11])=[C:7]([CH:9]=1)[NH2:8].[CH2:13]([OH:15])[CH3:14]>>[CH2:13]([O:15][C:3]1[CH:4]=[CH:5][C:6]([N+:10]([O-:12])=[O:11])=[C:7]([CH:9]=1)[NH2:8])[CH3:14]Participants
4
Conditions
- Temperature
- 80 °C
Procedure
A mixture of sodium metal (1.86 g, 80.9 mmol) and ethanol (65 mL) was stirred at ambient temperature until all of the sodium metal had been consumed. 5-Chloro-2-nitroaniline (4.64 g, 26.9 mmol) was added and the mixture was heated at 80° C. for 48 hours, cooled to room temperature, quenched with water, concentrated under vacuum, diluted with ethyl acetate, washed with water and brine, dried (MgSO4), filtered, and concentrated under vacuum. The residue was purified by column chromatography on silica gel with 7:3 hexane/ethyl acetate to provide 4.6 g (94%) of the desired product. MS (ESI) m/e 183 (M+H)+; 1H NMR (300 MHz, DMSO-d6) □ 7.90 (d, J=9.5 Hz, 1H), 7.46 (br s, 2H), 6.43 (d, J=2.7 Hz, 1H), 6.23 (dd, J=2.7, 9.5 Hz, 1H), 4.04 (q, J=7.1 Hz, 2H), 1.33 (t, J=7.0 Hz, 3H).