
To a solution of 3,8-dihydroxy-2,9-dimethyl deca-3,7-diene-5,6-dione 2 [1] (452 g, 2 mmol) in absolute ethanol (15 mL) was added the 4-methylorthophenylenediamine 1 (244 mg, 2 mmol) and the mixture was refluxed for 90 min [2] . The orange precipitate 3 was filtred off, washed with ethanol and dried in air.
Yield: (400 mg , 64 %).
Melting point: 98 - 99 °C (EtOH).
IR (KBr, cm-1): 2960 (CH of CH3) ; 1560 (C=O).
1H-NMR (200 MHz, CDCl3) d ppm: 14.66 (s, 2H, N-H); 14.46 (s, 2 H, N-H); 6.89 (m, 3H, CH Benz); 5.71 (s, 1H, =CH); 5.69 (s, 1H, =CH); 2.68 (m, 2H, C-H, J = 6.9 Hz); 2.32 (s, 3H, CH3 ); 1.9 (d, 12H, CH3, J = 6.9 Hz).
E. A: Anal. Calc. for C19H24N2O2: C 73.05, H 7.74, N 8.97; found : C 73.18, H 7.77, N 8.76.
Supplementary materials
Supplementary File 1Supplementary File 2Supplementary File 3References and notes:
- Bouabdallah, I.; Zidane, I.; Malek, F.; Touzani, R.; El Kodadi, M.; Ramdani, A. Molbank 2003, M 345.
- Touzani, R.; Ben-hadda, T.; El Kadiri, S.; Ramdani, A.; Maury, O.; Le Bozec, H.; Toupet, L.; Dixneuf, P.H. New J. Chem. 2001, 25, 391–395.
- Sample Availability: Available from the Authors.
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