The 1H NMR spectra for the synthesized compound were recorded on a Varian Unity-300 (300 MHz) in
DMSO-d6.
2-Aminocarbonylphenoxyacetic Acid (1). Salicylamide (34.3 g, 25 mmol) was added to a solution of
monochloroacetic acid (28.4 g, 300 mmol) in water (200 ml), and then a solution of NaOH (22.0 g, 550 mmol)
in water (200 ml) was added gradually with stirring to the suspension obtained. The mixture was heated up to
100°C for 3 h and acidified with 20% HCl until it tested as weakly acidic. After cooling, the precipitate was
filtered out, washed with water, and dried. Obtained 45.8 g (94%) of compound 1 as colorless thin needles;
1
mp 224-226°C (water). H NMR spectrum, δ, ppm: 4.75 (2H, s, CH2); 7.00-7.08 (2H, m, arom. protons);
7.34-7.48, 7.95-8.14 (4H, m, arom. protons + CONH2); 13.20 (1H, br. s, COOH). Found, %: C 55.02; H 4.80.
C9H9NO4. Calculated, %: C 55.38; H 4.65.
1,4-Benzoxazepine-3,5(2H,4H)-dione (2). SOCl2 (31.5 ml, 420 mmol) was added to a suspension of
acid 1 (40 g, 20 mmol) in toluene (150 ml), and the mixture was boiled for 5 h until evolution of HCl stopped.
19.3 g (53%) of compound 2 as yellowish needles; mp 155-157°C (toluene) precipitated out of the transparent
yellow-red solution upon cooling down to 0°C. 1H NMR spectrum, δ, ppm: 4.78 (2H, s, CH2); 7.17 (1H, d, 9-H);
7.31 (1H, t, 8-H); 7.62 (1H, dt, 7-H); 8.00 (1H, dd, 6-H); 11.20 (1H, s, NH). Found, %: C 60.64; H 3.52.
C9H7NO3. Calculated, %: C 61.02; H 3.98. A molecular ion peak [M]+ with m/z 176 (Irel, 12%) is observed in the
mass spectrum, which allows us to eliminate polymeric structures for compound 2.
2-Cyanophenoxyacetic Acid (3). Toluene (100 ml) was distilled off from the filtrate obtained in
synthesis of compound 2; hot water (150 ml) was added to the residue, and Na2CO3 was added in portions with
stirring until foaming stopped. The aqueous layer was removed and acidified with 20% HCl. 11.3 g (31%) of
compound 3 with mp 178-179°C (acetonitrile) precipitated. IR spectrum (vaseline oil), ν, cm-1: 2232 (CN).
1H NMR spectrum, δ, ppm: 4.80 (2H, s, CH2); 7.04-7.13 (2H, m, arom. protons); 7.54-7.67 (2H, m, arom.
protons); 13.02 (1H, br. s, COOH). Found, %: C 61.40; H 3.38. C9H7NO3. Calculated, %: C 61.02; H 3.98.
This research was done with the financial support of the Russian Foundation for Basic Research (grant
No. 02-03-81101 Bel 2002).
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