2-HYDROXY-1H-PYRROLO[3,2-B]PYRIDINE-3-CARBONITRILE synthesis
- Product Name:2-HYDROXY-1H-PYRROLO[3,2-B]PYRIDINE-3-CARBONITRILE
- CAS Number:32501-04-5
- Molecular formula:C8H5N3O
- Molecular Weight:159.14
87592-12-9
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Yield:32501-04-5 46%
Reaction Conditions:
Stage #1: ethyl 2-cyano-2-(3-aminopyrid-2-yl)acetate in xylene; for 16 h;Heating / reflux;
Stage #2: with sodium hydroxide;carbon dioxide in water at 0;
Steps:
1C EXAMPLE 1C; 2-Hydroxy-1H-pyrrolo[3,2-b]pyridine-3-carbonitrile
A mixture of cyano-(3-aminopyridin-2-yl)-acetic acid ethyl ester (4.80 g, 23.4 mmol) and xylene (150 mL) was heated to reflux for 16 h. The solution was cooled to 0° C. and filtered to give a dark tan solid. The residue was dissolved in sodium hydroxide solution (3%, 80 mL) and filtered through activated charcoal. Carbon dioxide was bubbled through the solution and filtration gave the title compound (1.71 g, 46%) as a pale solid. mp>250° C. (lit. value>325° C.; N. Finch, M. M. Robison, M. P. Valerio, J. Org. Chem., 1972, 37 (1), 51); 1H NMR (300 MHz, DMSO-d6) δ 6.60 (dd, J 7.5, 5.8, 1H), 6.88 (dd, J 7.5, 1.3, 1H), 7.59 (dd, J 5.8, 1.3, 1H); MS (ESI/APCI+) m/z 160 (M+H)+; MS (ESI/APCI-) m/z 158 (M-H)-
References:
US2004/192697,2004,A1 Location in patent:Page 17
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