反应详情

A stirred suspension of 3-nitrophthalic anhydride (0.24 g, 1.13 mmol) and 3-amino-3-(3-ethoxy-4-methoxyphenyl)propanenitrile (0.25 g, 1.13 mmol) in 6 mL of acetic acid was heated to reflux under nitrogen for 12 hours. The acetic acid was removed in vacuo to afford an orange gum which was dissolved in methylene chloride (10 mL) and was washed with a saturated aqueous solution of sodium bicarbonate (2×10 mL). The organic layer was separated and the aqueous layer was extracted with methylene chloride (10 mL). The combined organic extracts were dried over magnesium sulfate, filtered and concentrated in vacuo to afford a yellow oil. The crude product was purified by flash column chromatography (silica gel, 5% ethyl acetate/methylene chloride) and the resulting solid was dried in vacuo (60° C., <1 mm) to afford 0.25 g (56%) of 3-(3-nitrophthalimido)-3-(3-ethoxy-4-methoxyphenyl)propanenitrile as a yellow solid: mp 155.5°-157° C.; 1H NMR (CDCl3) δ 8.20-8.09 (m, 2 H), 8.02-7.86 (m, 1 H), 7.15-7.02 (m, 2 H), 6.88-6.76 (m, 1 H), 5.64 (dd, J=6.3, 10.6 Hz, 1 H), 4.09 (q, J=7 Hz, 2 H), 3.85 (s, 3 H), 3.84 (dd, J=10.6, 16.7 Hz, 1 H), 3.26 (dd, J=6.3, 16.7 Hz, 1 H), 1.46 (t, J=7 Hz, 3 H); 13C NMR (CDCl3) δ 165.3, 162.3, 150.1, 148.7, 144.9, 135.7, 133.5, 129.0, 128.1, 127.4, 123.2, 120.3, 116.6, 112.1, 111.5, 64.6, 55.9, 51.9, 20.9, 14.7; Anal. calcd for C20H17N3O6. Theoretical: C, 60.76; H, 4.33; N, 10.63. Found: C, 60.59; H, 4.22; N, 10.65.

1. temperaturewas heated
2. temperatureto reflux under nitrogen for 12 hours
3. customThe acetic acid was removed in vacuo
4. customto afford an orange gum which
5. washwas washed with a saturated aqueous solution of sodium bicarbonate (2×10 mL)
6. customThe organic layer was separated
7. extractionthe aqueous layer was extracted with methylene chloride (10 mL)
8. dry with materialThe combined organic extracts were dried over magnesium sulfate
9. filtrationfiltered
10. concentrationconcentrated in vacuo
11. customto afford a yellow oil
12. customThe crude product was purified by flash column chromatography (silica gel, 5% ethyl acetate/methylene chloride)
13. customthe resulting solid was dried in vacuo (60° C., <1 mm)