Page 7 of 11
The Journal of Organic Chemistry
2-(2-Hydroxy-5-iodophenyl)isoindoline-1,3-dione (2k). Brown
MHz, acetone-d6): = 8.71 (br, 1H), 7.81 (d, J = 7.6 Hz, 1H), 7.75
(s, 1H), 7.71 (d, J = 7.6 Hz, 1H), 7.35-7.27 (m, 2H), 7.05 (dd, J =
8.0, 1.2 Hz, 1H), 6.97 (ddd, J = 7.6, 7.6, 1.2 Hz, 1H), 2.56 (s, 3H)
ppm. 13C{1H} NMR (100 MHz, acetone-d6): = 168.0, 167.9,
154.9, 146.5, 135.6, 133.8, 131.3, 131.1, 130.9, 124.4, 123.9,
120.6, 117.5, 21.8 ppm. HRMS (ESI) calcd. for [M+Na]+
C15H11NO3Na 276.0631, found 276.0632 (0 ppm).
5-(tert-Butyl)-2-(2-hydroxyphenyl)isoindoline-1,3-dione (2s).
Colorless solid, yield = 87%, 77.0 mg. Mp: 116-119 oC. 1H NMR
(400 MHz, acetone-d6): = 7.96-7.95 (m, 2H), 7.86 (d, J = 8.4 Hz,
1H), 7.36-7.29 (m, 2H), 7.07 (dd, J = 8.4, 1.2 Hz, 1H), 6.98 (ddd,
J = 8.4, 8.4, 1.2 Hz, 1H), 1.44 (s, 9H) ppm. 13C{1H} NMR (100
MHz, acetone-d6): = 168.2, 167.8, 159.4, 154.9, 133.6, 132.1,
131.2, 131.1, 130.8, 123.9, 121.0, 120.54, 120.47, 117.5, 36.3, 31.4
ppm. HRMS (ESI) calcd. for [M+Na]+ C18H17NO3Na 318.1101,
found 318.1104 (1 ppm).
5-Fuloro-2-(2-hydroxyphenyl)isoindoline-1,3-dione (2t). Col-
orless solid, yield = 91%, 70.2 mg. Mp: 190-193 oC. 1H NMR (400
MHz, acetone-d6): = 8.00 (dd, J = 8.4, 4.4 Hz, 1H), 7.71-7.63 (m,
2H), 7.36-7.30 (m, 2H), 7.07 (dd, J = 8.0, 1.2 Hz, 1H), 6.98 (ddd,
J = 7.6, 7.6, 1.2 Hz, 1H) ppm. 13C{1H} NMR (100 MHz, acetone-
d6): = 167.2 (d, JC-F = 252.5 Hz), 166.9, 166.6 (d, JC-F = 2.9 Hz),
154.8, 136.3 (d, JC-F = 9.5 Hz), 131.3 (d, JC-F = 17.7 Hz), 129.4 (d,
JC-F = 2.8 Hz), 126.8 (d, JC-F = 9.5 Hz), 122.0 (d, JC-F = 23.8 Hz),
120.6, 120.2, 117.5, 111.6 (d, JC-F = 25.0 Hz) ppm. 19F{1H} NMR
(376 MHz, acetone-d6): δ = -104.5 ppm. HRMS (ESI) calcd. for
[M+Na]+ C14H8NO3FNa 280.0380, found 280.0382 (1 ppm).
2-(2-Hydroxyphenyl)-5-nitroisoindoline-1,3-dione (2u). Yel-
low solid, yield = 82%, 69.9 mg. 1H NMR (400 MHz, acetone-d6):
= 8.96 (br, 1H), 8.76 (dd, J = 8.4, 2.0 Hz, 1H), 8.64 (d, J = 2.0
Hz, 1H), 8.23 (d, J = 8.0 Hz, 1H), 7.39-7.33 (m, 2H), 7.09 (dd, J =
8.0, 1.2 Hz, 1H), 7.00 (ddd, J = 8.0, 8.0, 1.2 Hz, 1H) ppm. 13C{1H}
NMR (100 MHz, acetone-d6): = 166.2, 166.0, 154.7, 152.9,
137.8, 134.7, 131.6, 131.0, 130.4, 125.6, 120.7, 119.8, 119.0, 117.6
ppm. MS (EI): m/z = 248 (M+, 100), 204 (85), 104 (30) 76 (84), 50
(31). The spectral data match those previously reported.44
solid, yield = 85%, 93.0 mg. Mp > 250 oC dec. 1H NMR (400 MHz,
acetone-d6): = 9.10 (br, 1H), 7.96-7.90 (m, 4H), 7.71 (d, J = 2.4
Hz, 1H), 7.66 (dd, J = 8.8, 2.4 Hz, 1H), 6.92 (d, J = 8.8 Hz, 1H)
ppm. 13C{1H} NMR (100 MHz, acetone-d6): = 167.6, 155.2,
140.0, 139.7, 135.3, 133.4, 124.1, 122.2, 119.9, 80.2 ppm. HRMS
(ESI) calcd. for [M+Na]+ C14H8NO3INa 387.9441, found 387.9443
(0 ppm).
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2-(6-Fluoro-2-hydroxyphenyl)isoindoline-1,3-dione (2l). Yel-
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low solid, yield = 42%, 32.4 mg. Mp: 204-207 C. H NMR (400
MHz, acetone-d6): = 9.31 (br, 1H), 8.01-7.94 (m, 4H), 7.39 (dd,
J = 8.4, 6.8 Hz, 1H), 6.92 (d, J = 8.4 Hz, 1H), 6.84 (dd, J = 8.4, 8.4
Hz, 1H) ppm. 13C{1H} NMR (100 MHz, acetone-d6): = 167.2,
160.6 (d, JC-F = 246.5 Hz), 156.9 (d, JC-F = 3.6 Hz), 135.6, 133.2,
131.9 (d, JC-F = 10.5 Hz), 124.4, 113.3 (d, JC-F = 3.0 Hz), 108.8 (d,
JC-F = 16.0 Hz), 107.3 (d, JC-F = 20.0 Hz) ppm. 19F{1H} NMR (376
MHz, acetone-d6): δ = -122.0 ppm. HRMS (ESI) calcd. for
[M+Na]+ C14H8NO3FNa 280.0380, found 280.0383 (1 ppm).
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2-(2-Hydroxy-6-methylphenyl)isoindoline-1,3-dione
(2m).
Colorless solid, yield = 28%, 21.1 mg. Mp: 145-148 oC. 1H NMR
(400 MHz, acetone-d6): = 8.75 (br, 1H), 7.97-7.91 (m, 4H), 7.22
(dd, J = 8.0, 8.0 Hz, 1H), 6.88 (dd, J = 8.0, 8.0 Hz, 2H), 2.14 (s,
3H) ppm. 13C{1H} NMR (100 MHz, acetone-d6): = 167.9, 155.1,
139.4, 135.3, 133.4, 130.8, 124.1, 122.0, 119.7, 114.8, 17.9 ppm.
HRMS (ESI) calcd. for [M+Na]+ C15H11NO3Na 276.0631, found
276.0635 (1 ppm).
2-(2-Hydroxyphenyl)-4-methylisoindoline-1,3-dione (2n). Col-
orless solid, yield = 90%, 68.3 mg. Mp: 187-190 oC. 1H NMR (400
MHz, acetone-d6): = 8.77 (br, 1H), 7.74-7.72 (m, 2H), 7.65-7.63
(m, 1H), 7.35-7.29 (m, 2H), 7.07 (dd, J = 8.0, 1.2 Hz, 1H), 6.98
(ddd, J = 7.6, 7.6, 1.2 Hz, 1H), 2.70 (s, 3H) ppm. 13C{1H} NMR
(100 MHz, acetone-d6): = 168.7, 167.8, 154.9, 138.6, 137.2,
134.6, 133.8, 131.3, 131.1, 129.9, 121.6, 120.5, 120.4, 117.5, 17.6
ppm. HRMS (ESI) calcd. for [M+Na]+ C15H11NO3Na 276.0631,
found 276.0634 (1 ppm).
4-Fluoro-2-(2-hydroxyphenyl)isoindoline-1,3-dione (2o). Col-
orless solid, yield = 84%, 64.7 mg. Mp: 200-203 oC. 1H NMR (400
MHz, acetone-d6): = 8.82 (br, 1H), 7.95 (ddd, J = 8.0, 8.0, 4.4 Hz,
1H), 7.79 (d, J = 7.2 Hz, 1H), 7.63 (dd, J = 8.8, 8.8 Hz, 1H), 7.37-
7.32 (m, 2H), 7.07 (dd, J = 8.0, 1.2 Hz, 1H), 6.99 (ddd, J = 7.6, 7.6,
1.2 Hz, 1H) ppm. 13C{1H} NMR (100 MHz, acetone-d6): = 166.8
(d, JC-F = 3.1 Hz), 164.6 (d, JC-F = 1.6 Hz), 158.4 (d, JC-F = 261.1
Hz), 154.8, 138.1 (d, JC-F = 7.7 Hz), 135.7 (d, JC-F = 1.8 Hz), 131.3
(d, JC-F = 18.7 Hz), 123.2 (d, JC-F = 19.8 Hz), 120.6, 120.4 (d, JC-F
= 3.7 Hz), 120.0, 119.0 (d, JC-F = 12.5 Hz), 117.6 ppm. 19F{1H}
NMR (376 MHz, acetone-d6): δ = -115.7 ppm. HRMS (ESI) calcd.
for [M+Na]+ C14H8NO3FNa 280.0380, found 280.0383 (1 ppm).
4-Chloro-2-(2-hydroxyphenyl)isoindoline-1,3-dione (2p). Col-
orless solid, yield = 71%, 58.1 mg. Mp: 209-212 oC. 1H NMR (400
MHz, acetone-d6): = 8.82 (br, 1H), 7.91-7.84 (m, 3H), 7.37-7.32
(m, 2H), 7.07 (dd, J = 8.0, 1.2 Hz, 1H), 6.99 (ddd, J = 7.6, 7.6, 1.2
Hz, 1H) ppm. 13C{1H} NMR (100 MHz, acetone-d6): = 166.5,
165.5, 154.9, 136.6, 136.5, 135.6, 131.39, 131.36, 131.2, 129.0,
122.8, 120.6, 120.0, 117.6 ppm. HRMS (ESI) calcd. for [M+Na]+
C14H8NO3ClNa 296.0085, found 296.0086 (0 ppm).
2-(2-Hydroxyphenyl)hexahydro-1H-isoindole-1,3(2H)-dione
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(2v). Colorless solid, yield = 91%, 66.9 mg. Mp: 232-235 C. H
NMR (400 MHz, acetone-d6): = 8.62 (br, 1H), 7.25 (ddd, J = 8.0,
8.0, 1.6 Hz, 1H), 7.09 (dd, J = 8.0, 1.6 Hz, 1H), 6.99 (d, J = 8.0 Hz,
1H), 6.91 (dd, J = 7.6, 7.6 Hz, 1H), 3.13-3.07 (m, 2H), 1.91-1.86
(m, 4H), 1.50-1.47 (m, 4H) ppm. 13C{1H} NMR (100 MHz, ace-
tone-d6): = 179.1, 154.2, 130.8, 130.5, 121.5, 120.5, 117.3, 41.0,
24.6, 22.6 ppm. HRMS (ESI) calcd. for [M+Na]+ C14H15NO3Na
268.0944, found 268.0947 (1 ppm).
1-(2-Hydroxyphenyl)pyrrolidine-2,5-dione (2w). Yellow solid,
yield = 89%, 33.9 mg. 1H NMR (400 MHz, acetone-d6): = 8.47
(br, 1H), 7.28-7.24 (m, 1H), 7.08 (dd, J = 8.0, 1.6 Hz, 1H), 6.98
(dd, J = 8.4, 1.2 Hz, 1H), 6.91 (ddd, J = 7.6, 7.6, 1.2 Hz, 1H), 2.84
(s, 4H) ppm. 13C{1H} NMR (100 MHz, acetone-d6): = 177.2,
154.2, 130.9, 130.5, 121.3, 120.5, 117.5, 29.4 ppm. MS (EI): m/z =
191 (M+, 100), 146 (88), 136 (54), 109 (100), 55 (84). The spectral
data match those previously reported.45
1-(2-Hydroxyphenyl)-3-methyl-1H-pyrrole-2,5-dione
(2x).
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Colorless solid, yield = 89%, 54.2 mg. H NMR (400 MHz, ace-
tone-d6): = 8.61 (br, 1H), 7.28 (ddd, J = 8.0, 8.0, 2.0 Hz, 1H),
7.15 (dd, J = 8.0, 2.0 Hz, 1H), 7.00 (dd, J = 8.0, 1.2 Hz, 1H), 6.92
(ddd, J = 7.6, 7.6, 1.2 Hz, 1H), 6.62 (q, J = 2.0 Hz, 1H), 2.11 (d, J
= 2.0 Hz, 3H) ppm. 13C{1H} NMR (100 MHz, acetone-d6): =
171.5, 170.4, 154.9, 147.0, 131.2, 130.9, 128.7, 120.52, 120.47,
117.4, 11.0 ppm. MS (EI): m/z = 203 (M+, 94), 159 (100), 133 (44),
68 (80), 52 (40). The spectral data match those previously re-
ported.36
2-(2-Hydroxyphenyl)-4-nitroisoindoline-1,3-dione (2q). Color-
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less solid, yield = 76%, 64.8 mg. Mp: 226-229 C. H NMR (400
MHz, acetone-d6): = 8.87 (br, 1H), 8.30-8.25 (m, 2H), 8.18 (dd,
J = 7.6, 7.6 Hz, 1H), 7.38-7.34 (m, 2H), 7.08 (ddd, J = 7.6, 1.2, 1.2
Hz, 1H), 6.99 (ddd, J = 7.6, 7.6, 1.2 Hz, 1H) ppm. 13C{1H} NMR
(100 MHz, acetone-d6): = 165.9, 163.3, 154.8, 146.1, 137.1,
135.2, 131.6, 131.1, 129.1, 127.6, 124.4, 120.7, 119.7, 117.7 ppm.
HRMS (ESI) calcd. for [M+Na]+ C14H8N2O5Na 307.0325, found
307.0327 (0 ppm).
2-(2-Hydroxyphenyl)-1H-benzo[de]isoquinoline-1,3(2H)-di-
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2-(2-Hydroxyphenyl)-5-methylisoindoline-1,3-dione (2r). Col-
one (2y). Colorless solid, yield = 85%, 59.8 mg. H NMR (400
orless solid, yield = 93%, 70.6 mg. Mp: 216-219 oC. 1H NMR (400
MHz, DMSO-d6): = 9.62 (br, 1H), 8.50 (d, J = 7.6 Hz, 4H), 7.90
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