反应详情

To 4-imidazol-1-yl-2-methyl-6-nitro-phenylamine (350 mg, 1.61 mmol) and 10% Palladium on carbon (40 mg) were added degassed methanol (5 mL) and TFA (5 drops). The reaction mixture was flushed and evacuated with hydrogen/vacuum line, stirred at room temperature for 14 h under hydrogen atmosphere (hydrogen balloon). The dark reaction mixture was filtered through a pad of celite and rinsed with methanol. Concentration of the filtrate gave the residue, which was diluted with water, and extracted with ethyl acetate. The combined organic layers were washed with saturated NaHCO3, and brine and dried over Na2SO4. Concentration to dryness gave the title compound (275 mg, 91%) as a solid. 1H NMR (300 MHz, CD3OD) δ 7.87 (1H, s), 7.34 (1H, s), 7.05 (1H, s), 6.72 (1H, d, J=2.4 Hz), 6.65 (1H, d, J=2.4 Hz) 2.21 (3H, s). LCMS (M+H)+ m/z 189 (t=0.23 min.). Procedure for the Preparation of 3,4-diamino-5-methyl-benzonitrile

1. customdegassed methanol (5 mL) and TFA (5 drops)
2. customThe reaction mixture was flushed
3. customevacuated with hydrogen/vacuum line
4. customThe dark reaction mixture
5. filtrationwas filtered through a pad of celite
6. washrinsed with methanol
7. customConcentration of the filtrate gave the residue, which
8. extractionextracted with ethyl acetate
9. washThe combined organic layers were washed with saturated NaHCO3, and brine
10. dry with materialdried over Na2SO4
11. concentrationConcentration to dryness