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M. Adib et al.
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(14) General Procedure for the Preparation of Compounds 3 and
5, Exemplified with 3a
In a 10 mL sealable tube, benzyl alcohol (2a, 0.216 g, 2 mmol),
Aliquat 336 (0.121 g, 0.3 mmol), and K2S2O8 (0.675 g, 2.5 mmol)
were added to a solution of isoquinoline (1a, 0.129 g, 1.0 mmol)
in MeCN (3 mL). The resultant mixture was heated at 80 °C for 2
h. After completion of the reaction, as indicated by TLC, the
reaction mixture was cooled to ambient temperature and
treated with sat. aq NaHCO3 (10 mL). The mixture was extracted
with EtOAc (3 × 10 mL), and the combined organic layers were
dried over Na2SO4, filtered, and the solvent was evaporated
under vacuum. The residue was purified by column chromatog-
raphy using n-hexane–EtOAc (8:1) as eluent to afford 3a.
(Isoquinolin-1-yl)(phenyl)methanone (3a)
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1
Yield: 0.198 g (85%); white solid; mp 74–75 °C. H NMR (300.1
MHz, CDCl3): δ = 7.47 (dd, J = 7.7, 7.4 Hz, 2 H, 2 × CH), 7.60–7.63
(m, 2 H, 2 × CH), 7.75 (t, J = 7.5 Hz, 1 H, CH), 7.81 (d, J = 5.9 Hz, 1
H, CH), 7.94 (d, J = 8.6 Hz, 1 H, CH), 7.96 (d, J = 7.7 Hz, 2 H, 2 ×
(8) Reux, B.; Nevalainen, T.; Raitio, K. H.; Koskinen, A. M. P. Bioorg.
Med. Chem. 2009, 17, 4441.
CH), 8.20 (d, J = 8.6 Hz, 1 H, CH), 8.54 (d, J = 5.9 Hz, 1 H, CH). 13
C
NMR (75.1 MHz, CDCl3): δ = 123.1, 125.8, 126.1, 127.3, 127.9,
128.3, 130.9, 131.2, 133.5, 136.4, 136.6, 141.7, 155.5, 194.1.
(4-Chlorophenyl)(quinolin-2-yl)methanone (5c)
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Chem. 2015, 80, 5625. (d) Wan, M.; Lou, H.; Liu, L. Chem.
Commun. 2015, 51, 13953. (e) Chen, J.; Wan, M.; Hua, J.; Sun, Y.;
Lv, Z.; Li, W.; Liu, L. Org. Biomol. Chem. 2015, 13, 11561.
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Yield 0.187 g (70%); white solid; mp 128–129 °C. 1H NMR (300.1
MHz, CDCl3): δ = 7.45 (d, J = 8.5 Hz, 2 H, 2 × CH), 7.62 (t, J = 8.0
Hz, 1 H, CH), 7.75 (t, J = 7.2 Hz, 1 H, CH), 7.88 (d, J = 7.5 Hz, 1 H,
CH), 8.12 (d, J = 8.7 Hz, 1 H, CH), 8.19 (d, J = 7.9 Hz, 1 H, CH),
8.24 (d, J = 8.5 Hz, 2 H, 2 × CH), 8.35 (d, J = 8.7 Hz, 1 H, CH). 13C
NMR (75.1 MHz, CDCl3): δ = 119.9, 127.5, 128.5, 128.9, 129.1,
130.3, 130.6, 133.3, 134.6, 137.0, 140.1, 147.2, 154.3, 193.1.
© Georg Thieme Verlag Stuttgart · New York — Synlett 2016, 27, A–E