B. Das et al. / Tetrahedron Letters 49 (2008) 2225–2227
2227
applications in organic synthesis have not yet been fully
explored. In the present conversion, it has efficiently been
utilized for the preparation of N-formyl anilines. The
experimental procedure is highly convenient. The struc-
10.79 (br s, 1H), 8.77 (d, J = 8.0 Hz, 1H), 8.54 (br s, 1H),
7.80–7.44 (m, 7H), 7.08 (t, J = 7.0 Hz, 1H); EI-MS:
m/z = 225; Anal. Calcd for C H NO : C, 74.66; H,
1
4
11
2
4.88; N, 6.22. Found: C, 74.72; H, 4.91; N, 6.26.
tures of the products were established from their spectral
1
(
H NMR and MS) and analytical data.
Acknowledgements
3
. General experimental procedure
The authors thank CSIR and UGC, New Delhi, for
financial assistance.
To a mixture of aniline (1 mmol) and HCOOH
(
3 mmol), PEG-400 (2 g) was added. The mixture was stir-
References and notes
red at room temperature and the progress of the reaction
was monitored by TLC. After completion, the mixture
was diluted with water (10 mL) and extracted with EtOAc
1
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(
3 Â 10 mL). The combined organic layer was dried over
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anhydrous Na SO and concentrated. The residue was
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N-formyl aniline.
2
4
5
453.
3
4
. Downie, I. M.; Earle, M. J.; Heaney, H.; Shuhaibar, K. F.
Tetrahedron 1993, 49, 4015.
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Kobayashi, S.; Yasuda, M.; Hachiya, I. Chem. Lett. 1996, 407.
. Martrniez, J.; Laur, J. Synthesis 1982, 979.
1
The spectral (IR, H NMR and MS) and analytical data
1
of novel compounds e, h and q are given below. In the H
NMR spectra of all these compounds, the formyl proton
appeared as cis to the proton of the –NH-group.
5
6
. Strazzolini, P.; Giumanimi, A. G.; Cauci, S. Tetrahedron 1990, 46,
1
081.
7
. Neveux, M.; Bruneaum, C.; Dixneuf, P. H. J. Chem. Soc., Perkin
Trans. 1 1991, 1197.
3
.1. N-(2,4-Dichlorophenyl) formamide (entry e)
8
. Duczek, W.; Deutsch, J.; Vieth, S.; Niclas, H.-J. Synthesis 1996,
3
7.
9. Green, T. W.; Wuts, P. G. M. Protecting Groups in Organic synthesis,
rd ed.; Wiley-Interscience: New York, 1999.
0. Reddy, P. G.; Kumar, G. D. K.; Baskaran, S. Tetrahedron Lett. 2000,
1, 9149.
11. Mihara, M.; Ishino, Y.; Minakara, S.; Komatsu, M. Synthesis 2003,
317.
2. Luca, L. D.; Giacomelli, G.; Porcheddu, A.; Salaris, M. Synlett 2004,
570.
3. Desai, B.; Danks, T. N.; Wagner, G. Tetrahedron Lett. 2005, 46,
55.
14. Hosseini-Sarvari, M.; Sharghi, H. J. Org. Chem. 2006, 71, 6652.
White solid. mp 57–58 °C. IR (KBr): 3242, 2903, 1665,
À1
1
1
(
(
527, 1395, 1293 cm ; H NMR (CDCl , 200 MHz): 9.52
3
3
br s, 1H), 8.38 (br s, 1H), 8.28 (d, J = 8.0 Hz, 1H), 7.39
d, J = 2.0 Hz, 1H), 7.22 (dd, J = 8.0, 2.0 Hz, 1H); EI-
1
4
MS: m/z = 189, 191, 193; Anal. Calcd for C H NOCl : C,
7
5
2
2
4
4.24; H, 2.62; N, 7.33. Found: C, 43.89; H, 2.56; N, 7.39.
1
1
2
3
.2. N-(2-Acetylphenyl) formamide (entry h)
9
White solid; mp 79–80 °C. IR (KBr): 3254, 2925, 1695,
À1
1
1
1
5. Pratap, T. V.; Baskaran, S. Tetrahedron Lett. 2001, 42, 1983.
6. Das, B.; Reddy, V. S.; Krishnaiah, M. Tetrahedron Lett. 2006, 47,
1
1
7
527, 1395, 1293 cm
;
H NMR (CDCl , 200 MHz):
3
1.62 (br s, 1H), 8.79 (d, J = 8.0 Hz, 1H), 8.52 (br s, 1H),
.90 (d, J = 8.0 Hz, 1H), 7.49 (t, J = 8.0 Hz, 1H), 7.08 (t,
8
471.
7. Das, B.; Reddy, V. S.; Tehseen, F.; Krishnaiah, M. Synthesis 2007,
66.
1
J = 8.0 Hz, 1H), 2.60 (s, 3H); EI-MS: m/z = 163; Anal.
6
Calcd for C H NO : C, 66.25; H, 5.52; N, 8.58. Found:
C, 66.30; H, 5.48; N, 8.52.
18. Jung, S. H.; Ahn, J. H.; Park, S. K.; Choi, J.-K. Bull. Korean Chem.
Soc. 2002, 23, 149.
9
9
2
1
9. Dickerson, T. J.; Reed, N. N.; Janda, K. D. Chem. Rev. 2002, 102,
325.
3
3
.3. N-(2-Benzoylphenyl) formamide (entry q)
2
0. Chandrasekhar, S.; Narasihmulu, Ch.; Sultana, S. S.; Reddy, N. R.
Chem. Commun. 2003, 9, 1716.
Light yellow viscous oil. IR (KBr): 3319, 2924, 1699,
21. Kamal, A.; Reddy, D. R.; Rajendar. Tetrahedron Lett. 2006, 47,
261.
À1
1
2
1
638, 1514, 1262 cm
;
H NMR (CDCl , 200 MHz):
3