Some common heterocyclic compound, 82172-73-4, name is O-(2-Methoxyethyl)hydroxylamine hydrochloride, molecular formula is C3H10ClNO2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. HPLC of Formula: C3H10ClNO2
Example 6-7 [0239] The Z isomer of cyclopropyl(6,6-diphenyl-6,7-dihydro-1H-indazol-3-yl)methanone O-(2-methoxyethyl)oxime may be prepared in the following manner: [0240] A suspension of 0.74 g of cyclopropyl(6,6-diphenyl-6,7-dihydro-1H-indazol-3-yl)methanone and 0.70 g of O-(2-methoxyethyl)hydroxylamine hydrochloride in 50 cm3 of pyridine is refluxed for about 7 hours. The solution obtained is concentrated to dryness under reduced pressure (13 kPa). The residue is taken up in 150 cm3 of dichloromethane. The solution is washed with three times 80 cm3 of water, dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure (13 kPa). The mixture of the Z and E isomers is separated by flash chromatography on a column of silica [eluent: dichloromethane/methanol (98/2 by volume)], collecting 60 cm3 fractions. [0241] Fractions 111 to 135 are combined and concentrated to dryness under reduced pressure (13 kPa). 0.37 g of the Z isomer of cyclopropyl(6,6-diphenyl-6,7-dihydro-1H-indazol-3-yl)methanone O-(2-methoxyethyl)oxime, corresponding to Example 6-7A, is thus obtained in the form of a resin, the characteristics of which are as follows: [0242] 1H NMR spectrum: (300 MHz, (CD3)2SO d6 with addition of a few drops of CD3COOD d4, delta in ppm): from 0.70 to 0.90 (mt: 4H); 1.81 (mt: 1H); 3.22 (s: 3H); 3.40 (s: 2H); 3.56 (t, J=5.5 Hz: 2H); 4.13 (t, J=5.5 Hz: 2H); 6.25 (d, J=10 Hz: 1H); 6.89 (d, J=10 Hz: 1H); from 7.10 to 7.30 (mt: 10H). [0243] IR spectrum (solvent CCl4) [0244] 3459; 3316; 2932; 2882; 1597; 1492; 1446; 1386; 1291; 1145; 1126; 1069; 1027; 1007; 952; 894; 700; 683 and 541 cm-1 [0245] O-(2-Methoxyethyl)hydroxylamine hydrochloride may be prepared as described by Dae-Kee Kim et al., J. Med. Chem., 40, 15, 1997, 2363-2373.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 82172-73-4, its application will become more common.
Reference:
Patent; Aventis Pharma S.A.; US2004/162276; (2004); A1;,
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