2,5-Dimethylaniline → N-(2,5-dimethylphenyl)-3-oxobutanamide
Reaction equation
[CH3:1][C:2]1[CH:8]=[CH:7][C:6]([CH3:9])=[CH:5][C:3]=1[NH2:4].[O:10]=[C:11]([CH3:18])[CH2:12][C:13](OCC)=[O:14]>>[CH3:1][C:2]1[CH:8]=[CH:7][C:6]([CH3:9])=[CH:5][C:3]=1[NH:4][C:13](=[O:14])[CH2:12][C:11](=[O:10])[CH3:18]Participants
3
Procedure
A mixture of 2,5-dimethylaniline (1.00 g, 8.25 mmol) and ethyl 3-oxobutanoate (1.0 mL, 1.0 eq) was microwaved at 180° C. for 5 minutes. After the reaction mixture was cooled to room temperature, it was triturated with hexane. The resulting precipitate was filtered and dried under high vacuum to yield the desired title compound. Spectroscopic data: 1H NMR (300 MHz, CDCl3) δ ppm 2.28 (s, 3 H) 2.32 (s, 3 H) 2.34 (s, 3 H) 3.63 (s, 2 H) 6.88 (d, J=7.62 Hz, 1 H) 7.07 (d, J=7.62 Hz, 1 H) 7.75 (s, 1 H) 9.00-9.12 (m, 1 H).
Workup
- customwas microwaved at 180° C. for 5 minutes
- customit was triturated with hexane
- filtrationThe resulting precipitate was filtered
- customdried under high vacuum