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A. V. Aksenov et al.
LETTER
N-(3,4-Dimethoxyphenyl)acetamide (3d)
(7) Ohwada, T.; Yamagata, N.; Shudo, K. J. Am. Chem. Soc.
1991, 113, 1364.
1
2
1
Mp 129–131 °C (H O); lit. mp 130–131 °C. H NMR (300
2
MHz, CDCl ): d = 2.15 (3 H, s, COMe), 3.84 (3 H, s, OMe),
(8) Preparation of Compounds 6a–d: General Procedure
Corresponding aromatic compound 3a–d (1 mmol) and
nitroethane (2a, 0.083 g, 1.1 mmol) in PPA (3–4 g) was
stirred at 105–110 °C for 3–5 h (Table 1). Reaction mixture
3
3
.86 (3 H, s, OMe), 6.77 (1 H, d, J = 8.6 Hz, H-5), 6.89 (1 H,
dd, J = 8.6, 2.4 Hz, H-6), 7.30 (1 H, d, J = 2.4 Hz, H-2), 7.55
(
1
1 H, br s, NH). IR (KBr): n = 3276 (NH), 1653 (CONH),
max
–
1
606 (CONH) cm . Anal. Calcd (%) for C H NO : C,
was poured in H O (30 mL) with intense stirring, then boiled
1
0
13
3
2
61.53; H, 6.71; N, 7.17. Found: C, 61.65; H, 6.64; N, 7.09.
under reflux for 2 h. The resulting mixture was extracted by
N-Phenylacetamide (3e)
CH Cl (3 × 50 mL). The aqueous layer was made alkaline
2
2
1
1
1
Mp 113–115 °C (H O); lit. mp 113.5–114.5 °C. H NMR
with ammonia to pH 8–9, the precipitate after cooling
2
(
300 MHz, DMSO-d ): d = 2.04 (3 H, s, COMe), 7.01 (1 H,
(crystals or oil) was extracted by CH Cl (10 × 30 mL). The
6
2
2
dt, J = 7.5, 1.2 Hz, H-4), 7.28 (2 H, dd, J = 8.4, 7.5 Hz, H-3/
), 7.58 (2 H, dd, J = 8.4, 1.2 Hz, H-2/6), 9.94 (1 H, br s,
solution was evaporated under vacuum and purified by
crystallization (compounds 6a,b were purified by their
hydrochlorides’ crystallization from ethanol).
4-Aminophenol (6a)
5
NH). IR (KBr): n = 3296 (NH), 1662 (CONH), 1600
max
–1
(CONH) cm . Anal. Calcd (%) for C H NO: C, 71.09; H,
8 9
1
7
6
.71; N, 10.36. Found: C, 71.26; H, 6.63; N, 10.28.
Mp 188–190 °C (alcohol–H O); lit. mp 187–190 °C. Anal.
2
N-(4-Methylphenyl)acetamide (3f)
Calcd (%) for C H NO: C, 66.04; H, 6.47; N, 12.84. Found:
6
7
1
1
1
Mp 147–148 °C (H O); lit. mp 147–148.5 °C. H NMR
C, 66.23; H, 6.44; N, 12.76 (HCl); mp 303–305 °C (alcohol;
2
1
(
300 MHz, DMSO-d ): d = 2.01 (3 H, s, COMe), 2.23 (3 H,
with sublimation). H NMR (300 MHz, DMSO-d ): d = 6.87
6
6
s, Me), 7.08 (2 H, d, J = 8.1 Hz, H-3/5), 7.45 (2 H, d, J = 8.1
(d, J = 8.9 Hz, 2 H, H-3/5), 7.21 (d, J = 8.9 Hz, 2 H, H-2/6),
9.88 (br s, 1 H, OH); 10.19 (br s, 3 H, NH3).
4-Anisidine (6b)
Hz, H-2/6), 9.84 (1 H, br s, NH). IR (KBr): n = 3300
max
–
1
(NH), 1664 (CONH), 1604 (CONH) cm . Anal. Calcd (%)
1
8
for C H NO: C, 72.46; H, 7.43; N, 9.39. Found: C, 72.65;
Mp 57–59 °C; lit. mp 56–59 °C. Anal. Calcd (%) for
9
11
H, 7.37; N, 9.31.
C H NO: C, 68.27; H, 7.37; N, 11.37. Found: C, 68.44; H,
7
9
N-(3,4-Dimethylphenyl)acetamide (3g)
7.30; N, 11.31 (HCl); mp 217–220 °C (alcohol; with
1
3
1
1
Mp 94–96 °C (H O); lit. mp 94–95 °C. H NMR (300
sublimation). H NMR (300 MHz, DMSO-d ): d = 3.71 (s, 3
2
6
MHz, DMSO-d ): d = 2.05 (3 H, s, COMe), 2.26 (6 H, s,
H, Me), 7.0 (d, J = 8.8 Hz, 2 H, H-3/5), 7.35 (d, J = 8.8 Hz,
2 H, H-2/6), 10.44 (br s, 3 H, NH3).
6
Me), 6.97 (1 H, dd, J = 8.1, 2.0 Hz, H-6), 7.04 (1 H, d,
J = 2.0 Hz, H-2), 7.21 (1 H, d, J = 8.1 Hz, H-5), 9.73 (1 H,
2,5-Dimethoxyaniline (6c)
Mp 80–81 °C (PE); lit. mp 80 °C. H NMR (300 MHz,
1
9
1
br s, NH). IR (KBr): n = 3300 (NH), 1660 (CONH), 1601
max
–1
(
CONH) cm . Anal. Calcd (%) for C H NO: C, 73.59; H,
CDCl ): d = 3.71 (s, 3 H, OMe), 3.76 (br s, 2 H, NH ), 3.78
1
0
13
3
2
8.03; N, 8.58. Found: C, 73.72; H, 7.96; N, 8.49.
(s, 3 H, OMe), 6.24 (dd, J = 8.7, 2.8 Hz, 1 H, H-4), 6.31 (d,
J = 2.8 Hz, 1 H, H-6), 6.67 (d, J = 8.7 Hz, 1 H, H-3). Anal.
Calcd (%) for C H NO : C, 62.73; H, 7.24; N, 9.14. Found:
N-(4-Methoxyphenyl)butyramide (3h)
1
Mp 88–90 °C (EtOH). H NMR (300 MHz, DMSO-d ): d =
6
8
11
2
0.84 (3 H, t, J = 7.5 Hz, Me), 1.61 (2 H, m, CH ), 2.08 (2 H,
C, 62.90; H, 7.18; N, 9.05.
2
t, J = 6.7 Hz, CH ), 3.72 (3 H, s, OMe), 6.82 (2 H, d, J = 8.9
Hz, H-3/5), 7.46 (2 H, d, J = 8.9 Hz, H-2/6), 9.72 (1 H, br s,
3,4-Dimethoxyaniline (6d)
Mp 85–87 °C (PE); lit. mp 86 °C. H NMR (300 MHz,
2
2
0
1
NH). IR (KBr): n = 3265 (NH), 1656 (CONH), 1604
CDCl ): d = 3.44 (br s, 2 H, NH ), 3.79 (s, 3 H, OMe), 3.82
max
3
2
–
1
(
CONH) cm . Anal. Calcd (%) for C H NO : C, 68.37; H,
(s, 3 H, OMe), 6.15 (d, J = 2.1 Hz, 1 H, H-2), 6.31 (dd,
J = 6.0, 2.1 Hz 1 H, H-6), 6.70 (d, J = 6.0 Hz, 1 H, H-5).
Anal. Calcd (%) for C H NO : C, 62.73; H, 7.24; N, 9.14.
1
1
15
2
7.82; N, 7.25. Found: C, 68.52; H, 7.77; N, 7.18.
N-(9-Anthracenyl)acetamide (3i)
8
11
2
1
4
Mp 276–278 °C (EtOH); lit. mp 277 °C. For spectral data,
Found: C, 62.86; H, 7.19; N, 9.02.
see ref. 15.
N-(3-Indolyl)acetamide (3j)
Mp 162–163 °C (EtOH–H O); lit. mp 162–163 °C. H
(9) A reaction with benzene and toluene was carried out in a
sealed tube.
(10) Owsley, D. C.; Bloomfield, J. J. Synthesis 1977, 118.
1
5
1
2
NMR (300 MHz, acetone-d ): d = 2.17 (3 H, s, COMe), 7.01
(11) Baessler, A. Chem. Ber. 1884, 17, 2118.
(12) Mizuno, M.; Inagaki, A.; Yamashita, M.; Soma, N.; Maeda,
Y.; Nakatani, H. Tetrahedron 2006, 62, 4065.
6
(
1 H, m, ArH), 7.12 (1 H, m, ArH), 7.38 (1 H, d, J = 8.3 Hz,
ArH), 7.74 (1 H, d, J = 8.1 Hz, ArH), 7.89 (1 H, d, J = 2.4
Hz, ArH), 9.32 (1 H, br s, NH), 10.06 (1 H, br s, NH). IR
(13) Mann, F. G.; Porter, G. W. G. J. Chem. Soc. 1947, 910.
(14) Rigaudy, J.; Ahond, M.; Barcelo, J.; Valt-Taphanel, M.-H.
Bull. Soc. Chim. France 1981, 2, 223.
–1
(
KBr): nmax = 3306 (NH), 1661 (CONH), 1603 (CONH) cm .
Anal. Calcd (%) for C H N O: C, 68.95; H, 5.79; N, 16.08.
1
0
10
2
Found: C, 69.12; H, 5.71; N, 15.99.
(7)-Acetoaminoperimidine (3k)
Mp 225–226 °C (EtOAc); lit. mp 225–226 °C. For spectral
(15) Velezheva, V. S.; Yarosh, A. V.; Kozik, T. A.; Suvorov, N.
N. Chem. Heterocycl. Compd. (Engl. Transl.) 1978, 1217.
(16) Aksenov, A. V.; Lyakhovnenko, A. S.; Andrienko, A. V.;
Levina, I. I. Tetrahedron Lett. 2010, 51, 2406.
6
1
6
data, see ref. 17.
(
6) See references in: (a) Berrocal, M. V.; Gil, M. V.; Roman,
E.; Serrano, J. A. Tetrahedron 2002, 58, 5327. (b) White,
E. H.; Considine, W. J. J. Am. Chem. Soc. 1958, 80, 626.
(17) Davis, R.; Muchowski, J. M. Synthesis 1982, 987.
(18) Casarini, A.; Dembech, P.; Lassari, D.; Marini, E.; Reginato,
G.; Ricci, A.; Seconi, G. J. Org. Chem. 1993, 58, 5620.
(19) Blackhall, A.; Tomson, R. H. J. Chem. Soc. 1954, 3916.
(20) Frisch, K. C.; Bogert, M. T. J. Org. Chem. 1943, 8, 331.
(
c) Cherest, M.; Lusinchi, X. Tetrahedron 1986, 42, 3825.
(
d) Rank, W.; Baer, H. Can. J. Chem. 1971, 49, 3236.
Synlett 2010, No. 17, 2628–2630 © Thieme Stuttgart · New York