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J. Kuwabara et al.
Letter
Synlett
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(17) Typical Procedure for the Nitrile Hydration of Tolunitrile
(1a)
To a nitromethane (0.10 mL) solution of 4-methylbenzonitrile
(1a, 30 mg, 0.256 mmol) were added H2O (1.0 mL), DBU (78 mg,
0.512 mmol), copper(I) iodide (9.8 mg, 0.0512 mmol), and
cesium(I) carbonate (42 mg, 0.128 mmol) at room temperature.
The reaction mixture was heated at 100 °C for 1 h and then
poured into water (50 mL). The organic layer was separated, and
the aqueous layer was extracted with AcOEt. The combined
organic layer was dried over MgSO4. The solvent was removed
under reduced pressure. The residue was purified by prepara-
tive TLC on silica gel eluting with AcOEt–n-hexane (1:1) to give
4-methylbenzamide (2a, 32 mg, 92%) as pale yellow powders.
1H NMR (400 MHz, CDCl3): δ = 2.40 (3 H, s, CH3), 6.10 (2 H, br s,
NH), 7.25 (2 H, d, J = 8.2 Hz, ArH), 7.71 (2 H, d, J = 8.2 Hz, ArH).
© Georg Thieme Verlag Stuttgart · New York — Synlett 2018, 29, A–E