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J. Cao et al. / Chinese Chemical Letters 21 (2010) 935–938
3. Conclusion
In summary, we have developed a ‘‘one-step’’ method for the synthesis of secondary aliphatic amine substituted
nitrobenzaldehyde. The reaction is environmentally friendly because of increasing synthetic efficiency and making
performance simple. Further investigation on the reaction of aromatic secondary amine with halogenated
nitrobenzaldehyde is undergoing.
Acknowledgments
We thank for financial support by the open project program of Key Laboratory of Environmentally Friendly
Chemistry and Applications of Ministry of Education of China (No. 09HJYH04) and Hunan Science & Technology
Department Project (No. 2009FJ3166).
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[10] Compound 1: 2-(N-piperidinyl)-5-nitrobenzaldehyde, Yellow solid, mp 111.2–111.8 8C. 1H NMR (CDCl3): d 10.07 (s, 1H), 8.62 (d, 1H), 8.28
(d, 1H), 7.09 (d, 1H), 3.32 (m, 4H), 1.76 (m, 6H). 13C NMR (CDCl3): d 188.5, 158.8, 140.5, 129.2, 127.8, 125.8, 118.2, 54.6, 26.8, 23.7. Found:
C, 61.56; H, 6.21; N, 12.01. Anal. Calcd. for C12H14N2O3: C, 61.53; H, 6.02; N, 11.96; O, 20.49; Compound 2: 2-(N-morpholinyl)-5-
nitrobenzaldehyde, Yellow solid, mp 114.1–114.4 8C. 1H NMR (CDCl3): d 10.12 (s, 1H), 8.65 (d, 1H), 8.34 (dd, 1H), 7.11 (d, 1H), 3.94 (t, 4H),
3.30 (t, 4H). 13C NMR (CDCl3): d 188.2, 157.8, 129.5, 129.0, 126.3, 118.2, 66.5, 53.3. Found: C, 55.98; H, 5.33; N, 11.93. Anal. Calcd. for
C11H12N2O4: C, 55.93; H, 5.12; N, 11.86; O, 27.09; Compound 3: 4-(N-piperidinyl)-3-nitrobenzaldehyde, Yellow oil, 1H NMR (CDCl3): d 9.83
(s, 1H), 8.26 (d, 1H), 7.90 (d, 1H), 7.14 (d, 1H), 3.24 (m, 4H), 1.72 (m, 6H). 13C NMR (CDCl3): d 188.7, 150.0, 141.6, 139.1, 138.0, 132.8,
126.7, 51.9, 25.6, 23.7. Found: C, 61.51; H, 6.26; N, 12.01. Anal. Calcd. for C12H14N2O3: C, 61.53; H, 6.02; N, 11.96; O, 20.49; Compound 4:
4-(N-morpholinyl)-3-nitrobenzaldehyde, Yellow oil. 1H NMR (CDCl3): d 9.88 (s, 1H), 8.29 (d, 1H), 7.97 (dd, 1H), 7.16 (d, 1H), 3.87 (t, 4H),
3.24 (t, 4H). 13C NMR (CDCl3): d 188.7, 149.4, 140.2, 133.4, 129.6, 128.3, 119.7, 66.3, 50.9. Found: C, 55.96; H, 5.32; N, 11.93. Anal. Calcd.
for C11H12N2O4: C, 55.93; H, 5.12; N, 11.86; O, 27.09; Compound 5: 5-(N-piperidinyl)-2-nitrobenzaldehyde, Orange solid, mp 95.2–96.4 8C,
1H NMR (CDCl3): d 10.48 (s, 1H), 8.04 (d, 1 H), 7.05 (d, 1 H), 6.87 (dd, 1H), 3.47 (m, 4H), 1.66 (m, 6H). 13C NMR (CDCl3): d 190.7, 154.3,
135.6, 128.2, 115.2, 112.5, 48.7, 25.6, 24.5. Found: C, 61.48; H, 6.10; N, 12.04. Anal. Calcd. for C12H14N2O3: C, 61.53; H, 6.02; N, 11.96; O,
20.49. Compound 6: 5-(N-morpholinyl)-2-nitrobenzaldehyde. Orange solid, mp 155.1–156.8 8C. 1H NMR (CDCl3): d 10.52 (s, 1H), 8.12 (d,
1H), 7.17 (d, 1H), 6.95 (dd, 1H), 3.86 (t, 4H,), 3.43 (t, 4H). 13C NMR (CDCl3): d 190.2, 154.1, 135.7, 128.6, 115.2, 112.4, 66.3, 52.8. Found: C,
56.01; H, 5.33; N, 11.91. Anal. Calcd. for C11H12N2O4: C, 55.93; H, 5.12; N, 11.86; O, 27.09.