* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
With sodium dithionite In ethanol; water at 65℃; for 4 h;
To a suspension of 2, 4-dichloro-6-nitrophenol (60.0 g, 288 mmol) in ethanol (250 mL) and water (250 mL) was added portionwise sodium hydrosulfite (251 g, 1.44 mmol). The mixture was stirred at 65°C for 4 h. The mixture was concentrated in vacuo, diluted with saturated aqueous sodium hydrogen carbonate solution (500 mL) , extracted with ethyl acetate (200 mL X 4 ) and washed with brine. The organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel EPO <DP n="81"/>eluting with a 0-50percent ethyl acetate/n-hexane gradient mixture. The filtrate was concentrated in vacuo to give the solid, which was washed with n-hexane to give the title compound (30.6 g, 172 mmol, 60percent) as a colorless powder. 1H NMR (CDCl3) δ 3.92 (s, 2H), 5.36 (s, IH), 6.59 (d, J = 2.1 Hz, IH), 6.71 (d, J = 2.1 Hz, IH). MS Calcd.: 177; MS Found: 178 (M+H) .
Reference:
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[3] Patent: WO2008/51533, 2008, A2, . Location in patent: Page/Page column 79-80
[4] Patent: US2002/156081, 2002, A1,
[5] Patent: US6921763, 2005, B2,
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[12] Patent: US5215925, 1993, A,
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[14] Patent: US2005/124667, 2005, A1, . Location in patent: Page/Page column 12
2
[ 609-89-2 ]
[ 7772-99-8 ]
[ 527-62-8 ]
Reference:
[1] Patent: US5886044, 1999, A,
[2] Patent: US5780483, 1998, A,
[3] Patent: US6262113, 2001, B1,
3
[ 609-89-2 ]
[ 527-62-8 ]
Reference:
[1] Patent: US4723010, 1988, A,
4
[ 139137-46-5 ]
[ 527-62-8 ]
Reference:
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5
[ 120-83-2 ]
[ 527-62-8 ]
Reference:
[1] Justus Liebigs Annalen der Chemie, 1870, vol. Suppl.7, p. 185
6
[ 108-95-2 ]
[ 527-62-8 ]
Reference:
[1] Justus Liebigs Annalen der Chemie, 1870, vol. Suppl.7, p. 185
5-((3,5-dichloro-2-hydroxyphenyl)amino)methyl-2-cyanopyridine[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
53%
With sodium cyanoborohydride; acetic acid; In methanol; at 60℃;
Compound 21C (1 g, 7.57 mmol),2-Amino-4,6-dichlorophenol and acetic acid (10 drops) were dissolved in 30 mL of methanol.Sodium cyanoborohydride (2.38 g, 37.8 mmol) was added at room temperature with stirring.The reaction solution was stirred at 60 C overnight, and after cooling to room temperature, 100 mL of water was added.The precipitate is precipitated and filtered to obtain the target crude product.The crude product was isolated by reverse phase column chromatography to afford pale yellow compound 21 (1.2 g, 53% yield)