Page 7 of 12
The Journal of Organic Chemistry
o
NMR (101 MHz, CDCl3, 20 C) δ 151.9, 144.3, 115.2, 114.8,
55.9, 48.2, 38.4, 11.2. These spectroscopic data correspond
to reported data.23
N-methyl-N-propylaniline (2n). Purification by silica
gel column chromatography using ethyl
1
2
3
4
5
6
7
8
acetate/petroleum ether (1:80, v/v) gave yellow oil, 74 mg,
99%. 1H NMR (400 MHz, CDCl3, 20 oC) δ 7.14 (t, J = 8.0 Hz,
2H), 6.63-6.57 (m, 3H), 3.19 (t, J = 8.0 Hz, 2H), 2.85 (s, 3H),
1.57-1.48 (m, 2H), 0.84 (t, J = 7.4 Hz, 3H). 13C NMR (101
N-ethyl-N, 4-dimethylaniline (2h). Purification by
silica gel column chromatography using ethyl
acetate/petroleum ether (1:80, v/v) gave yellow oil, 72 mg,
97%. H NMR (400 MHz, CDCl3, 20 C) δ 7.06 (d, J = 8.3
Hz, 2H), 6.68 (d, J = 8.6 Hz, 2H), 3.38 (q, J = 7.1 Hz, 2H),
o
1
o
MHz, CDCl3, 20 C) δ 149.5, 129.2, 115.9, 112.2, 54.7, 38.4,
20.1, 11.7. These spectroscopic data correspond to reported
13
data.27
2.88 (s, 3H), 2.27 (s, 3H), 1.11 (t, J = 7.1 Hz, 3H). C NMR
(101 MHz, CDCl3, 20 oC) δ 147.4, 129.8, 125.6, 113.1, 47.3, 37.8,
20.3, 11.2. These spectroscopic data correspond to reported
data.23
N-methyl-N-isobutylaniline (2o). Purification by
silica gel column chromatography using ethyl
acetate/petroleum ether (1:80, v/v) gave yellow oil, 81 mg,
99%. 1H NMR (400 MHz, CDCl3, 20 oC) δ 7.21 (t, J = 8.0 Hz,
2H), 6.65 (t, J = 8.5 Hz, 3H), 3.08 (d, J = 7.2 Hz, 2H), 2.94
(s, 3H), 2.10-2.01 (m, 1H), 0.91 (d, J = 6.7 Hz, 6H). 13C NMR
(101 MHz, CDCl3, 20 oC) δ 149.7, 129.2, 115.7, 111.9, 61.0, 39.5,
27.5, 20.6. These spectroscopic data correspond to
reported data.28
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N-ethyl-N, 3-dimethylaniline (2i). Purification by
silica gel column chromatography using ethyl
acetate/petroleum ether (1:80, v/v) gave yellow oil, 71 mg,
95%. 1H NMR (400 MHz, CDCl3, 20 oC) δ 7.14 (t, J = 8.1 Hz,
1H), 6.59 (s, 3H), 3.39 (q, J = 7.1 Hz, 2H), 2.91 (s, 3H), 2.32
13
(s, 3H), 1.13 (t, J = 7.1 Hz, 3H). C NMR (101 MHz, CDCl3,
20 oC) δ 149.4, 138.9, 129.2, 117.2, 113.3, 109.8, 47.0, 37.6, 22.1,
11.4. These spectroscopic data correspond to reported
data.24
N-benzyl-N-methylaniline (2p). Purification by silica
gel
column
chromatography
using
ethyl
acetate/petroleum ether (1:80, v/v) gave yellow oil, 98 mg,
1
o
99%. H NMR (400 MHz, CDCl3, 20 C) δ 7.25-7.22 (m,
2H), 7.16-7.12 (m, 5H), 6.68 (d, J = 8.0 Hz, 2H), 6.63 (t, J =
N-ethyl-N, 2-dimethylaniline (2j). Purification by
silica gel column chromatography using ethyl
acetate/petroleum ether (1:80, v/v) gave yellow oil, 66 mg,
88%. 1H NMR (400 MHz, CDCl3, 20 oC) δ 7.22-7.17 (m, 2H),
7.08 (d, J = 7.1 Hz, 1H), 6.99 (t, J = 7.3 Hz, 1H), 2.95 (q, J =
7.1 Hz, 2H), 2.72 (s, 3H), 2.35 (s, 3H), 1.14 (t, J = 7.1 Hz, 3H).
13
7.3 Hz, 1H), 4.46 (s, 2H), 2.94 (s, 3H). C NMR (101 MHz,
CDCl3, 20 C) δ 148.9, 139.9, 129.4, 128.9, 128.7, 126.3, 116.3,
o
112.3, 54.9, 38.6, 33.0. These spectroscopic data correspond
to reported data.23
13C NMR (101 MHz, CDCl3, 20 C) δ 152.3, 133.2, 131.1, 126.4,
N, 2-dimethyl-N-propylaniline (2q). Purification by
silica gel column chromatography using ethyl
acetate/petroleum ether (1:80, v/v) gave yellow oil, 80 mg,
98%. 1H NMR (400 MHz, CDCl3, 20 oC) δ 7.18 (t, J = 8.8 Hz,
2H), 7.07 (d, J = 7.8 Hz, 1H), 6.97 (t, J = 7.3 Hz, 1H), 2.85 (t,
J = 7.4 Hz, 2H), 2.68 (s, 3H), 2.33 (s, 3H), 1.56 (dd, J = 14.8
Hz, J = 7.4 Hz, 2H), 0.92 (t, J = 7.4 Hz, 3H). HRMS
(ESI/TOF) Calcd for C11H18N [(M+H)+]: 164.1439, found:
164.1449. These spectroscopic data correspond to reported
data.27
o
122.8, 119.9, 50.6, 41.0, 18.4, 13.0. These spectroscopic data
correspond to reported data.24
N-ethyl-N-methylnaphthalen-1-amine
(2k).
Purification by silica gel column chromatography using
ethyl acetate/petroleum ether (1:80, v/v) gave yellow oil,
82 mg, 89%. 1H NMR (400 MHz, CDCl3, 20 oC) δ 8.25 (d, J
= 7.3 Hz, 1H), 7.83 (dd, J = 6.6 Hz, J = 2.6 Hz, 1H), 7.54 (d, J
= 8.2 Hz, 1H), 7.51-7.44 (m, 2H), 7.40 (t, J = 7.8 Hz, 1H), 7.11
(d, J = 7.4 Hz, 1H), 3.16 (q, J = 7.1 Hz, 2H), 2.88 (s, 3H), 1.22
(t, J = 7.1 Hz, 3H). 13C NMR (101 MHz, CDCl3, 20 oC) δ 150.4,
135.0, 129.7, 128.4, 125.8, 125.2, 124.1, 123.1, 115.5, 51.6, 41.4,
12.9. These spectroscopic data correspond to reported
data.25
1-ethylindoline (2r). Purification by silica gel column
chromatography using ethyl acetate/petroleum ether
(1:40, v/v) gave yellow oil, 71 mg, 97%. 1H NMR (400 MHz,
o
CDCl3, 20 C) δ 7.08 (t, J = 7.7 Hz, 2H), 6.66 (t, J = 7.1 Hz,
1H), 6.50 (d, J = 7.7 Hz, 1H), 3.88 (q, J = 7.0 Hz, 1H), 3.34 (t,
J = 8.3 Hz, 2H), 3.15 (q, J = 7.2 Hz, 2H), 2.97 (t, J = 8.2 Hz,
2H), 1.26 (t, J = 7.0 Hz, 1H), 1.21 (t, J = 7.2 Hz, 3H). 13C NMR
N, N-diethylaniline (2l). Purification by silica gel
column chromatography using ethyl acetate/petroleum
ether (1:80, v/v) gave yellow oil, 70 mg, 94%. 1H NMR (400
MHz, CDCl3, 20 oC) δ 7.23 (t, J = 3.5 Hz, 2H), 6.72-6.65 (m,
3H), 3.40-3.30 (m, 4H), 1.20-1.12 (m, 6H). 13C NMR (101
o
(101 MHz, CDCl3, 20 C) δ 152.5, 130.4, 127.4, 124.5, 117.6,
107.3, 52.4, 43.3, 28.6, 12.1. These spectroscopic data
o
correspond to reported data.23
MHz, CDCl3, 20 C) δ 148.0, 129.4, 115.5, 112.0, 44.5, 12.7.
These spectroscopic data correspond to reported data.23
1-ethyl-2-methylindoline (2s). Purification by silica
gel
column
chromatography
using
ethyl
N-ethyl-N-isopropylaniline (2m). Purification by
silica gel column chromatography using ethyl
acetate/petroleum ether (1:80, v/v) gave yellow oil, 81 mg,
99%. 1H NMR (400 MHz, CDCl3, 20 oC) δ 7.17-7.12 (m, 2H),
6.68 (d, J = 8.2 Hz, 2H), 6.58 (t, J = 7.2 Hz, 1H), 4.01-3.94
(m, 1H), 3.17 (q, J = 7.0 Hz, 2H), 1.14-1.08 (m, 9H). 13C NMR
(101 MHz, CDCl3, 20 oC) δ 149.7, 129.2, 115.7, 111.9, 61.1, 39.5,
27.5, 20.6. HRMS (ESI/TOF) Calcd for C11H18N [(M+H)+]:
164.1439, found: 164.1447. These spectroscopic data
correspond to reported data.26
acetate/petroleum ether (1:40, v/v) gave white solid, 72
o
1
mg, 90%, mp: 36.5-38.7 C. H NMR (400 MHz, CDCl3, 20
oC) δ 7.04 (dd, J = 14.1 Hz, J = 7.1 Hz, 2H), 6.61 (t, J = 7.1 Hz,
1H), 6.41 (d, J = 7.8 Hz, 1H), 3.75-3.69 (m, 1H), 3.32-3.22 (m,
1H), 3.19-3.07 (m, 2H), 2.59 (dd, J = 15.3 Hz, J = 9.7 Hz, 1H),
1.30 (d, J = 6.1 Hz, 3H), 1.12 (t, J = 7.2 Hz, 3H). 13C NMR (101
o
MHz, CDCl3, 20 C) δ 152.0, 129.2, 127.5, 124.2, 117.1, 106.6,
58.8, 39.9, 37.5, 19.5, 11.4. These spectroscopic data
correspond to reported data.29
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