反应详情

16 (340 mg, 0.7 mmol) was added to a solution of methyl(triphenylphosphoranylidene)acetate (2|57 mg, 0.77 mmol) in toluene (30 mL) and the reaction mixture was heated to reflux for 3 days. The solvent was removed after cooled to room temperature. Ethyl acetate (10 mL) was added to the residue and the resulted precipitate 17 was filtered. MS (ion spray) (M+H) 259. Without further purification 17 was dissolved in DMF (3 mL) and methanol (5 mL) was added. 3N NaOH solution (2 mL) was added and the reaction mixture was stirred overnight. The solvent was removed and water (10 mL) was added. The solution was neutralized using 20% HCl. The resulting precipitate was filtered and washed with water. 44 mg (26% yield) of yellow solid 18 was obtained. mp: 238°-239° C. 1H NMR (DMSO-d6, ppm): 12.25 (brs, 1 H, COOH), 11.42 (s, 1 H, NH), 9.74 (s, 1 H, NH), 7.88 (s, 1 H, Ar--H), 7.55-7.50 (d, 1 H, J=16.0 Hz, CH=CH), 7.28 (s, 2 H, Ar--H) 6.80 (d, 1 H, J=2.0 Hz, Ar--H), 6.44-6.40 (d, 1 H, J=15.8 Hz, CH=CH), 2.03 (s, 3 H, CH3), Anal. (C13H12N2O3 0.3H2O), C, H, N.

1. temperaturethe reaction mixture was heated
2. temperatureto reflux for 3 days
3. customThe solvent was removed
4. additionEthyl acetate (10 mL) was added to the residue
5. filtrationthe resulted precipitate 17 was filtered
6. customWithout further purification 17
7. dissolutionwas dissolved in DMF (3 mL)
8. additionmethanol (5 mL) was added
9. addition3N NaOH solution (2 mL) was added
10. customThe solvent was removed
11. additionwater (10 mL) was added
12. filtrationThe resulting precipitate was filtered
13. washwashed with water