2,3-Dimethylaniline → HCID 178425510, compound

Participants

Reaction Conditions

Reaction Steps

2,3 Dimethylaniline (Aldrich, 236 mg, 1.95 mmol), imidazoline-2-sulfonic acid (292 mg, 1.95 mmol, (Compound 7 obtained as described above)) and CH3CN (4ml) were placed in a thick-walled glass tube and sealed with a TEFLON™ screw-cap. The reactants were heated to 155° C. for 6 hours The reaction was worked up as described for Compound 4 and chromatographed (SiO2 ; 70:30 CHCl3 /CH3OH saturated with NH3) to yield a light yellow oil which was recrystallized (hexane/isopropanol to yield 61 mg (17%) of the title compound as an off-white crystalline solid: mp 141°-144° C.; 1H NMR (300 MHz, CDCl3) & 6.98 (m, 1H); 6.80 (m, 2H), 5.31 (br, 2H); 3.42 (s, 4H); 2.31 (s, 3H); 2.12 (s, 3H); Mass spectrum m/e 189.1259 (C11H15N 3 requires 189.1266). Alternatively, and preferably alcohols, most preferably isobutanol, are used instead of CH3CN in this reaction.

Provenance & Evidence