Table 3 Reaction of different CH-acids and aldehydes with sodium
cyanide in water at 70 ◦
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C
Entry
1
CH-acid
Aldehyde
Product
Yield (%)
90
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3i
2
3
3j
95
85
3k
either electron-donating or electron-withdrawing substituents,
suggesting that this method can be used to synthesize a large
variety of compounds. It has therefore been demonstrated that
using water as the solvent is ideally suited for the synthesis of
alkyl nitriles. Furthermore, in this green synthetic protocol, the
solvent water itself catalyzed the reaction by hydrogen bonding,
thus avoiding the use of any other catalysts thus making the
work up procedure easier.
Experimental
Typical procedure: preparation of sodium 1,2,3,4-tetrahydro-
2,4-dioxopyrimidin-5-yl-6-oxide)-2-(4-hydroxyphenyl)acetoni-
trile (3a). A solution of barbituric acid (0.13 g, 1 mmol) and
4-hydroxybenzaldehyde (0.12 g, 1 mmol) in H2O (10 mL) was
stirred at 70 ◦C. After 30 min, sodium cyanide (0 05 g, 1 mmol)
was added and stirred for 3 h at 70 ◦C. After completion of the
reaction, as indicated by TLC, the solvent was evaporated. The
residue was washed with ethyl acetate and recrystallized in ethyl
acetate to give pure product 3a as a white powder (0.28 g, yield
99%). mp 240 ◦C. IR (KBr) (nmax/cm-1): 3184, 2272, 1708, 1603.
MS, m/z (%): 258 (M+ - Na, 5), 228 (7), 146 (15), 143 (20), 126
1
(30), 101 (40), 83 (100). H NMR (300 MHz, DMSO-d6): dH
(ppm) 5.13 (1H, s, CH–CN), 6.63 (2H, d, 3JHH = 8.4 Hz, H–Ar),
3
7.16 (2H, d, JHH = 8.4 Hz, H–Ar), 9.25 (3H, br s, 2NH and
OH).13C NMR (75 MHz, DMSO-d6): dC (ppm) 30.2 (CH–CN),
82.2 (C C–ONa), 115.1, 122.2, 128.6, 129.6, 152.5 (C–Ar and
CN), 156.4, 163.7 (C O). Anal. Calcd for C12H8N3NaO4: C,
51.25; H, 2.87; N, 14.94;. Found: C, 51.45; H, 2.95; N, 15.01.
Acknowledgements
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We gratefully acknowledge financial support from the Research
Council of Razi University.
Notes and references
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