The Journal of Organic Chemistry
Article
N-(4-Methoxyphenyl)-1-(p-tolyl)methanimine 3r.39 Following
the general procedure, 3r was purified by neutral alumina column
chromatography using a mixture of ethyl acetate and heptane (1:15)
as the eluent. Gray solid (92 mg, 82%). 1H NMR (400 MHz, CDCl3):
δ 8.45 (s, 1H), 7.80 (d, J = 8.1 Hz, 2H), 7.29−7.23 (m, 4H), 6.94 (d,
J = 8.9 Hz, 2H), 3.84 (s, 3H), 2.43 (s, 3H). 13C{1H} NMR (101
MHz, CDCl3): δ 158.5, 158.2, 145.2, 141.6, 134.0, 129.6, 128.7,
122.3, 114.5, 55.6, 21.7. GC−MS: m/z (%): 225 (M+, 85), 210 (100),
181 (10), 167 (10), 155 (10), 91 (10), 77 (15), 64 (10), 51 (5).
1-(4-Isopropylphenyl)-N-(4-methoxyphenyl)methanimine 3s.40
Following the general procedure, 3s was purified by neutral alumina
column chromatography using a mixture of ethyl acetate and heptane
(1:30) as the eluent. White solid (86 mg, 68%). 1H NMR (400 MHz,
CDCl3): δ 8.45 (s, 1H), 7.82 (d, J = 8.1 Hz, 2H), 7.33 (d, J = 8.1 Hz,
2H), 7.22 (d, J = 8.8 Hz, 2H), 6.93 (d, J = 8.8 Hz, 2H), 3.83 (s, 3H),
3.04−2.90 (m, 1H), 1.29 (d, J = 6.9 Hz, 6H). 13C{1H} NMR (101
MHz, CDCl3): δ 158.7, 158.3, 152.6, 145.3, 134.3, 128.9, 127.0,
122.3, 114.5, 55.7, 34.4, 24.0. GC−MS: m/z (%): 253 (M+, 100), 238
(65), 222 (15), 196 (15), 119 (10), 77 (15), 64 (5).
(%): 247 (M+, 35), 245 (M+, 90), 230 (100), 167 (20), 92 (10), 77
(15), 64 (10), 51 (5).
1-(2-Bromophenyl)-N-(4-methoxyphenyl)methanimine 3y.44
Following the general procedure, 3y was purified by neutral alumina
column chromatography using a mixture of ethyl acetate and heptane
1
(1:20) as the eluent. Brown solid (125 mg, 86%). H NMR (400
MHz, CDCl3): δ 8.90 (s, 1H), 8.25 (dd, J = 7.8, 1.7 Hz, 1H), 7.63
(dd, J = 8.0, 1.0 Hz, 1H), 7.42 (t, J = 7.5 Hz, 1H), 7.35−7.29 (m,
3H), 6.98 (d, J = 8.9 Hz, 2H), 3.87 (s, 3H). 13C{1H} NMR (101
MHz, CDCl3): δ 158.8, 157.2, 144.6, 134.9, 133.3, 132.1, 128.9,
127.8, 126.0, 122.7, 114.6, 55.6. GC−MS: m/z (%): 291 (M+, 95),
289 (M+, 100) 275 (80), 167 (50), 139 (20), 77 (20), 63 (20), 51
(10).
N-(4-Methoxyphenyl)-1-(4-(trifluoromethyl)phenyl)methanimine
3z.42 Following the general procedure, 3z was purified by neutral
alumina column chromatography using a mixture of ethyl acetate and
1
heptane (1:15) as the eluent. White solid (113 mg, 81%). H NMR
(400 MHz, CDCl3): δ 8.53 (s, 1H), 8.00 (d, J = 8.2 Hz, 2H), 7.72 (d,
J = 8.2 Hz, 2H), 7.28 (d, J = 8.9 Hz, 2H), 6.95 (d, J = 8.9 Hz, 2H),
3.84 (s, 3H). 13C{1H} NMR (101 MHz, CDCl3): δ 159.0, 156.4,
144.2, 139.7, 132.5 (q, J = 32.3 Hz), 128.8, 125.8 (q, J = 3.8 Hz),
124.1 (q, J = 273.0 Hz), 122.5, 114.6, 55.7. 19F NMR (376 MHz,
CDCl3): δ −62.8. GC−MS: m/z (%): 279 (M+, 85), 264 (100), 235
(10), 209, (5), 167 (10), 134 (10), 92 (10), 77 (15), 64 (15), 50 (5).
4-(((4-Methoxyphenyl)imino)methyl)benzonitrile 3aa.43 Follow-
ing the general procedure, 3aa was purified by neutral alumina
column chromatography using a mixture of ethyl acetate and heptane
N-(4-Methoxyphenyl)-1-(o-tolyl)methanimine 3t.41 Following
the general procedure, 3t was purified by neutral alumina column
chromatography using a mixture of ethyl acetate and heptane (1:20)
as the eluent. White solid (80 mg, 71%). 1H NMR (400 MHz,
CDCl3): δ 8.78 (s, 1H), 8.07 (dd, J = 7.6, 1.3 Hz, 1H), 7.37−7.27 (m,
2H), 7.23 (d, J = 8.9 Hz, 3H), 6.95 (d, J = 8.9 Hz, 2H), 3.84 (s, 3H),
2.59 (s, 3H). 13C{1H} NMR (101 MHz, CDCl3): δ 158.3, 157.3,
145.7, 138.4, 134.5, 131.1, 130.8, 127.8, 126.5, 122.3, 114.5, 55.7,
19.5. GC−MS: m/z (%): 225 (M+, 50), 208 (100), 194 (20), 180
(15), 165 (35), 116(65), 77 (55), 64 (30), 51 (15).
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(1:10) as the eluent. Gray solid (57 mg, 48%). H NMR (400 MHz,
CDCl3): δ 8.52 (s, 1H), 7.99 (d, J = 8.3 Hz, 2H), 7.74 (d, J = 8.3 Hz,
2H), 7.28 (d, J = 8.9 Hz, 2H), 6.95 (d, J = 8.9 Hz, 2H), 3.85 (s, 3H).
13C{1H} NMR (101 MHz, CDCl3): δ 159.2, 155.5, 143.8, 140.4,
132.6, 129.0, 122.7, 118.7, 114.7, 114.1, 55.7. GC−MS: m/z (%): 236
(M+, 85), 221 (100), 192 (20), 140 (10), 92 (10), 77 (15), 64 (15),
50 (5).
1-(4-Fluorophenyl)-N-(4-methoxyphenyl)methanimine 3u.39
Following the general procedure, 3u was purified by neutral alumina
column chromatography using a mixture of ethyl acetate and heptane
1
(1:20) as the eluent. Gray solid (90 mg, 79%). H NMR (400 MHz,
CDCl3): δ 8.44 (s, 1H), 7.91−7.87 (m, 2H), 7.23 (d, J = 8.9 Hz, 2H),
7.17−7.13 (m, 2H), 6.94 (d, J = 8.9 Hz, 2H), 3.83 (s, 3H). 13C{1H}
NMR (101 MHz, CDCl3): δ 164.6 (d, J = 251.6 Hz), 158.5, 156.9,
144.8, 133.0 (d, J = 3.1 Hz), 130.6 (d, J = 8.7 Hz), 122.3, 116.0 (d, J =
22.0 Hz), 114.5, 55.6. 19F NMR (376 MHz, CDCl3): δ −108.7. GC−
MS: m/z (%): 229 (M+, 90), 214 (100), 185 (25), 159 (10), 133 (5),
107 (10), 92 (5), 77 (10), 64 (10), 51 (5).
N-(4-Methoxyphenyl)-3-phenylprop-2-en-1-imine 3ab.45 Follow-
ing the general procedure, 3ab was purified by neutral alumina
column chromatography using a mixture of ethyl acetate and heptane
1
(1:10) as the eluent. Gray solid (69 mg, 58%). H NMR (400 MHz,
CDCl3): δ 8.29 (m, 1H), 7.53 (dd, J = 7.7, 0.7 Hz, 2H), 7.42−7.30
(m, 3H), 7.25−7.07 (m, 4H), 6.92 (d, J = 8.9 Hz, 2H), 3.82 (s, 3H).
13C{1H} NMR (101 MHz, CDCl3): δ 159.6, 158.5, 144.7, 143.1,
135.9, 129.5, 129.0, 128.9, 127.5, 122.3, 114.5, 55.6. GC−MS: m/z
(%): 237 (M+, 100), 193 (10), 115 (55), 77 (20), 64 (10).
1-(2-Fluorophenyl)-N-(4-methoxyphenyl)methanimine 3v.42
Following the general procedure, 3v was purified by neutral alumina
column chromatography using a mixture of ethyl acetate and heptane
N-(4-Methoxyphenyl)-1-(pyridin-2-yl)methanimine 3ac.46 Fol-
lowing the general procedure, 3ac was purified by neutral alumina
column chromatography using a mixture of ethyl acetate and heptane
1
(1:20) as the eluent. Brown oil (39 mg, 34%). H NMR (400 MHz,
CDCl3): δ 8.80 (s, 1H), 8.18 (td, J = 7.6, 1.7 Hz, 1H), 7.43 (td, J =
7.3, 1.8 Hz, 1H), 7.29−7.21 (m, 3H), 7.12 (m, 1H), 6.94 (d, J = 8.9
Hz, 2H), 3.84 (s, 3H). 13C{1H} NMR (101 MHz, CDCl3): δ 162.9
(d, J = 253.0 Hz), 158.7, 151.4 (d, J = 4.9 Hz), 144.9, 132.6 (d, J = 5.8
Hz), 127.8 (d, J = 2.7 Hz), 124.6 (d, J = 3.5 Hz), 124.4 (d, J = 9.0
Hz), 122.5, 115.9 (d, J = 21.1 Hz), 114.5, 55.6. 19F NMR (376 MHz,
CDCl3): δ −121.5. GC−MS: m/z (%): 229 (M+, 85), 214 (100), 185
(25), 159 (5), 133 (10), 92 (10), 77 (15), 64 (15), 50 (5).
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(1:10) as the eluent. Brown oil (75 mg, 71%). H NMR (400 MHz,
CDCl3): δ 8.69 (m, 1H), 8.62 (s, 1H), 8.18 (d, J = 7.9 Hz, 1H), 7.78
(m, 1H), 7.35−7.28 (m, 3H), 6.94 (d, J = 8.9 Hz, 2H), 3.83 (s, 3H).
13C{1H} NMR (101 MHz, CDCl3): δ 159.1, 158.3, 155.0, 149.7,
143.8, 136.7, 124.9, 122.8, 121.7, 114.6, 55.6. GC−MS: m/z (%): 212
(M+, 100), 197 (30), 170 (25), 142 (20), 92 (25), 79 (45), 64 (25),
52 (15).
1-(4-Chlorophenyl)-N-(4-methoxyphenyl)methanimine 3w.39
Following the general procedure, 3w was purified by neutral alumina
column chromatography using a mixture of ethyl acetate and heptane
1-(Furan-2-yl)-N-(4-methoxyphenyl)methanimine 3ad.43 Fol-
lowing the general procedure, 3ad was purified by neutral alumina
column chromatography using a mixture of ethyl acetate and heptane
(1:10) as the eluent. Brown solid (69 mg, 69%). 1H NMR (400 MHz,
CDCl3): δ 8.31 (s, 1H), 7.60 (d, J = 1.5 Hz, 1H), 7.27 (d, J = 9.0 Hz,
2H), 6.97−6.88 (m, 3H), 6.55 (dd, J = 3.4, 1.8 Hz, 1H), 3.83 (s, 3H).
13C{1H} NMR (101 MHz, CDCl3): δ 158.5, 152.4, 145.8, 145.4,
144.3, 122.4, 115.6, 114.5, 112.2, 55.5. GC−MS: m/z (%): 201 (M+,
90), 186 (100), 157 (10), 130 (10), 103 (10), 92 (10), 77 (20), 64
(10), 51 (10).
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(1:20) as the eluent. White solid (106 mg, 86%). H NMR (400
MHz, CDCl3): δ 8.44 (s, 1H), 7.83 (d, J = 8.4 Hz, 2H), 7.43 (d, J =
8.4 Hz, 2H), 7.24 (d, J = 8.9 Hz, 2H), 6.94 (d, J = 8.9 Hz, 2H), 3.84
(s, 3H). 13C{1H} NMR (101 MHz, CDCl3): δ 158.6, 156.8, 144.6,
137.1, 135.1, 129.9, 129.2, 122.4, 114.6, 55.7. GC−MS: m/z (%): 247
(M+, 35), 245 (M+, 100), 230 (100), 201 (10), 167 (20), 77 (15), 64
(15).
1-(2-Chlorophenyl)-N-(4-methoxyphenyl)methanimine 3x.43
Following the general procedure, 3x was purified by neutral alumina
column chromatography using a mixture of ethyl acetate and heptane
(1:20) as the eluent. Yellow oil (109 mg, 88%). 1H NMR (400 MHz,
CDCl3): δ 8.95 (s, 1H), 8.24 (dd, J = 7.1, 2.4 Hz, 1H), 7.44−7.33 (m,
3H), 7.29 (d, J = 8.9 Hz, 2H), 6.95 (d, J = 8.9 Hz, 2H), 3.84 (s, 3H).
13C{1H} NMR (101 MHz, CDCl3): δ 158.8, 154.8, 144.8, 135.9,
133.6, 131.9, 130.0, 128.5, 127.2, 122.7, 114.7, 55.6. GC−MS: m/z
N-(4-Methoxyphenyl)-1-(thiophen-2-yl)methanimine 3ae.47 Fol-
lowing the general procedure, 3ae was purified by neutral alumina
column chromatography using a mixture of ethyl acetate and heptane
(1:20) as the eluent. Brown solid (73 mg, 67%). 1H NMR (400 MHz,
CDCl3): δ 8.58 (s, 1H), 7.47 (m, 2H), 7.23 (d, J = 8.9 Hz, 2H), 7.12
(dd, J = 5.0, 3.7 Hz, 1H), 6.92 (d, J = 8.9 Hz, 2H), 3.83 (s, 3H).
13C{1H} NMR (101 MHz, CDCl3): δ 158.4, 151.2, 144.5, 143.3,
H
J. Org. Chem. XXXX, XXX, XXX−XXX