The Journal of Organic Chemistry
Page 6 of 14
2.50 (q, J = 6.7 Hz, 2H). 13C NMR (100 MHz, CDCl3) δ
147.3, 135.6, 132.0, 117.4, 114.5, 108.9, 42.9, 33.5.
N-(but-3-en-1-yl)-4-nitroaniline (1n) Yellow solid, 38.4 mg,
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20% yield. H NMR (400 MHz, CDCl3) δ 8.09 (d, J = 9.2
Hz, 2H), 6.53 (d, J = 9.2 Hz, 2H), 5.87– 5.77 (m, 1H), 5.26 –
5.11 (m, 2H), 4.50 (s, 1H), 3.29 (dd, J = 12.1, 6.6 Hz, 2H),
2.43 (q, J = 6.7 Hz, 2H). 13C NMR (100 MHz, CDCl3) δ
153.3, 138.2, 134.9, 126.6, 118.2, 111.2, 42.3, 33.3.
N-(but-3-en-1-yl)-3-iodoaniline (1g) Colorless oil, 128.2
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mg, 47% yield. H NMR (500 MHz, CDCl3) δ 7.02 (d, J =
7.7 Hz, 1H), 6.99 – 6.92 (m, 1H), 6.88 (t, J = 8.0 Hz, 1H),
6.56 (dd, J = 8.2, 2.2 Hz, 1H), 5.82 (ddt, J = 17.0, 10.1, 6.8 Hz,
1H), 5.29 – 4.97 (m, 2H), 3.69 (s, 1H), 3.16 (dd, J = 11.9, 6.4
Hz, 2H), 2.39 (dt, J = 7.9, 6.1 Hz, 2H). 13C NMR (126 MHz,
CDCl3) δ 149.4, 135.4, 130.6, 126.1, 121.3, 117.4, 112.2, 95.3,
42.5, 33.4.
N-(but-3-en-1-yl)-2-(trifluoromethyl)aniline (1o) Colorless
oil, 131.3 mg, 61% yield. 1H NMR (400 MHz, CDCl3) δ 7.79
- 7.19 (m, 2H), 6.95 - 6.62 (m, 2H), 5.92-5.80 (m, 1H), 5.69
- 5.02 (m, 2H), 4.55 (s, 1H), 3.39 (t, J = 6.4 Hz, 2H), 2.59
(ddd, J = 6.7, 6.2, 1.2 Hz, 2H). 13C NMR (100 MHz, CDCl3)
δ 145.8, 135.2, 133.2, 126.8, 126.7, 124.0, 117.7, 115.9, 111.9, 42.5,
33.4. 19F NMR (376 MHz, CDCl3) δ -62.44.
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3-bromo-N-(but-3-en-1-yl)aniline (1h) Colorless oil,
115.3 mg, 51% yield. 1H NMR (500 MHz, CDCl3) δ 7.02 (t, J
= 8.0 Hz, 1H), 6.81 (d, J = 7.1 Hz, 1H), 6.75 (d, J = 1.7 Hz,
1H), 6.52 (dd, J = 8.2, 2.1 Hz, 1H), 5.75-5.63 (m, 1H), 5.15 (t,
J = 13.2 Hz, 2H), 3.74 (s, 1H), 3.17 (dd, J = 12.2, 6.4 Hz, 2H),
2.39 (q, J = 6.7 Hz, 2H). 13C NMR (126 MHz, CDCl3) δ
149.5, 135.4, 130.5, 123.3, 120.0, 117.4, 115.3, 111.6, 42.6, 33.4.
N-(but-3-en-1-yl)-3,5-bis(trifluoromethyl)aniline
(1p)
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Colorless oil, 113.3 mg, 40% yield. H NMR (400 MHz,
CDCl3) δ 7.04 (s, 1H), 6.83 (s, 2H), 5.72 (td, J = 16.8, 6.6 Hz,
1H), 5.16 - 5.03 (m, 2H), 4.01 (s, 1H), 3.14 (dd, J = 12.1, 6.3
Hz, 2H), 2.33 (q, J = 6.7 Hz, 2H), 1.45 (s, 2H). 13C NMR
(100 MHz, CDCl3) δ 148.3, 134.5, 124.5, 121.8, 117.5, 111.4,
109.7, 41.9, 32.8. 19F NMR (376 MHz, CDCl3) δ -63.54.
N-(but-3-en-1-yl)-2-iodo-4-methylaniline (1i) Colorless oil,
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206.7 mg, 72 % yield. H NMR (400 MHz, CDCl3) δ 7.50
N-(but-3-en-1-yl)-3-(trifluoromethyl)aniline (1q) Colorless
(d, J = 1.7 Hz, 1H), 7.02 (dd, J = 8.2, 1.7 Hz, 1H), 6.48 (d, J =
8.2 Hz, 1H), 5.85 (ddt, J = 17.1, 10.2, 6.9 Hz, 1H), 5.23 – 5.10
(m, 2H), 4.05 (s, 1H), 3.20 (t, J = 6.7 Hz, 2H), 2.43 (q, J =
6.8 Hz, 2H), 2.21 (s, 3H). 13C NMR (100 MHz, CDCl3) δ
144.9, 139.1, 135.3, 129.8, 127.8, 117.3, 110.5, 85.3, 43.3, 33.3,
19.6.
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oil, 116.2 mg, 54% yield. H NMR (400 MHz, CDCl3) δ
7.30 (dd, J = 9.2, 6.6 Hz, 1H), 6.97 (d, J = 7.6 Hz, 1H), 6.84
(s, 1H), 6.78 (d, J = 8.2 Hz, 1H), 5.87 (ddt, J = 17.0, 10.1, 6.8
Hz, 1H), 5.44 – 4.88 (m, 2H), 3.91 (s, 1H), 3.26 (s, 2H), 2.57
– 2.29 (m, 2H). 13C NMR (100 MHz, CDCl3) δ 148.4, 135.4,
131.7, 131.4, 129.6, 125.7, 123.0, 117.5, 115.8, 113.7, 113.7, 108.9,
108.9, 42.5, 33.4. 19F NMR (376 MHz, CDCl3) δ -62.90.
N-(but-3-en-1-yl)-4-(trifluoromethyl)aniline (1j) Colorless
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oil, 124.7 mg, 58% yield. H NMR (400 MHz, CDCl3) δ
N-(but-3-en-1-yl)-[1,1'-biphenyl]-4-amine (1r) Colorless oil,
160.8 mg, 72% yield. 1H NMR (400 MHz, CDCl3) δ 7.42 (d,
J = 7.8 Hz, 2H), 7.33 (d, J = 8.0 Hz, 2H), 7.27 (t, J = 7.4 Hz,
2H), 7.20 – 7.10 (m, 1H), 6.56 (d, J = 8.4 Hz, 2H), 5.86 –
5.61 (m, 1H), 5.03 (t, J = 14.5 Hz, 2H), 3.63 (s, 1H), 3.11 (t, J =
6.7 Hz, 2H), 2.29 (q, J = 6.6 Hz, 2H). 13C NMR (100 MHz,
CDCl3) δ 147.5, 141.1, 135.6, 130.1, 128.5, 127.8, 126.1, 125.9,
117.0, 113.0, 42.7, 33.5.
7.45 - 7.30 (m, 2H), 6.68 (d, J = 8.3 Hz, 2H), 6.59 (d, J = 8.5
Hz, 2H), 5.81 (dd, J = 17.1, 10.2 Hz, 2H), 5.14 (dd, J = 12.7,
11.0 Hz, 3H), 3.97 (s, 3H), 3.21 (t, J = 6.7 Hz, 3H), 2.39 (d, J
= 6.7 Hz, 3H). 13C NMR (100 MHz, CDCl3) δ 150.4, 135.2,
126.6, 126.5, 117.4, 112.0, 42.4, 33.3. 19F NMR (376 MHz,
CDCl3) δ -61.02.
N-(but-3-en-1-yl)-4-methoxyaniline (1k) Colorless oil, 108.1
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mg, 61% yield. H NMR (400 MHz, CDCl3) δ 6.80 (d, J =
N-(but-3-en-1-yl)-[1,1'-biphenyl]-2-amine (1s) Colorless oil ,
8.9 Hz, 2H), 6.60 (d, J = 8.9 Hz, 2H), 5.87 – 5.80 (m, 1H),
5.19 – 5.07 (m, 2H), 3.75 (s, 3H), 3.32 (s, 1H), 3.15 (t, J = 6.7
Hz, 2H), 2.38 (q, J = 6.7 Hz, 2H). 13C NMR (100 MHz,
CDCl3) δ 152.2, 142.6, 136.0, 117.1, 115.0, 114.3, 55.8, 43.9, 33.8.
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133.9 mg, 60% yield. H NMR (500 MHz, CDCl3) δ 7.48 –
7.31 (m, 5H), 7.28 – 7.21 (m, 1H), 7.10 (d, J = 7.4 Hz, 1H),
6.77 (t, J = 7.4 Hz, 1H), 6.73 – 6.68 (m, 1H), 5.94 – 5.50 (m,
1H), 5.00 (dd, J = 8.6, 6.5 Hz, 2H), 3.99 (s, 1H), 3.18 (dd, J =
11.8, 6.4 Hz, 2H), 2.32 (q, J = 6.7 Hz, 2H). 13C NMR (126
MHz, CDCl3) δ 145.0, 139.4, 135.6, 130.1, 129.4, 128.8, 128.7,
127.7, 127.1, 117.0, 116.8, 110.4, 42.8, 33.5.
4-(but-3-en-1-ylamino)benzonitrile (1l) Colorless oil, 86 mg,
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50% yield. H NMR (400 MHz, CDCl3) δ 7.41 (d, J = 8.8
Hz, 2H), 6.55 (d, J = 8.8 Hz, 2H), 5.80 (ddt, J = 17.1, 10.2,
6.8 Hz, 1H), 5.20 – 5.08 (m, 2H), 4.24 (s, 1H), 3.22 (t, J = 6.7
Hz, 2H), 2.39 (q, J = 6.7, 2H). 13C NMR (100 MHz, CDCl3)
δ 151.2, 135.0, 133.7, 120.5, 117.7, 112.2, 98.6, 42.0, 33.2.
1-(4-(but-3-en-1-ylamino)phenyl)ethanone (1t) Colourless
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oil, 125.1 mg, 66% yield. H NMR (400 MHz, CDCl3) δ
7.78 (d, J = 8.9 Hz, 2H), 6.52 (d, J = 8.8 Hz, 2H), 5.78 (ddt,
J = 17.1, 10.2, 6.8 Hz, 1H), 5.20 – 5.02 (m, 2H), 4.19 (s, 1H),
3.22 (t, J = 6.7 Hz, 2H), 2.46 (s, 3H), 2.37 (dtd, J = 6.8, 5.5,
1.3 Hz, 2H). 13C NMR (126 MHz, CDCl3) δ 196.1, 151.8, 134.9,
130.6, 126.5, 117.4, 111.2, 41.9, 33.1, 25.8.
N-(but-3-en-1-yl)-4-(trifluoromethoxy)aniline (1m)
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Colorless oil, 111 mg, 48% yield. H NMR (400 MHz,
CDCl3) δ 7.03 (d, J = 8.9 Hz, 2H), 6.60 (d, J = 9.0 Hz, 2H),
5.87 – 5.78 (m, 1H), 5.25 – 5.14 (m, 2H), 3.78 (s, 1H), 3.21 (t,
J = 6.7 Hz, 2H), 2.43 (q, J = 6.7 Hz, 2H). 13C NMR (100
MHz, CDCl3) δ 146.9, 140.3, 135.4, 124.5, 122.3, 121.9, 120.7
(q, J = 257 Hz), 119.4, 117.2, 116.8, 112.9, 42.8, 33.4. 19F NMR
(376 MHz, CDCl3) δ -58.31.
(3-(but-3-en-1-ylamino)phenyl)(phenyl)methanone
Light yellow solid, 158.3 mg, 63% yield. H NMR (400
MHz, CDCl3) δ 7.81 (d, J = 7.7 Hz, 2H), 7.57 (t, J = 7.4 Hz,
(1u)
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