ChemicalBook CAS DataBase List 4-hydroxythieno[3,2-c]pyridine-7-carbonitrile

4-hydroxythieno[3,2-c]pyridine-7-carbonitrile synthesis

5synthesis methods

Product Name:4-hydroxythieno[3,2-c]pyridine-7-carbonitrile
CAS Number:55040-34-1
Molecular formula:C8H4N2OS
Molecular Weight:176.2

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4-hydroxythieno[3,2-c]pyridine-7-carbonitrile

55040-34-1
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Yield:55040-34-1 78%

Reaction Conditions:

Stage #1: copper(I) cyanide;7-bromothieno[3,2-c]pyridine-4(5H)-one in DMF (N,N-dimethyl-formamide);Heating / reflux;
Stage #2: with hydrogenchloride;iron(III) chloride;water in DMF (N,N-dimethyl-formamide) at 20 - 70; for 0.5 h;

Steps:

1.1

Step 1: 7-Cyano-5H-thieno [3,2-c]pyridm-4-one; A solution of7-Bromo-5H-thieno[3,2-c]pyridin-4-one (2 g, 8.69 mmol, from Aldrich Chemical Co. ) and CuCN (1.68 g, 18.7 mmol) in DMF (30 ml) was refluxed overnight. The mixture was allowed to cool to room temperature and poured into an aqueous solution of FeCl3 (20 g), HCl (5.5 ml). The resulting mixture was stirred at 70 °C for 30 minutes. The suspension was filtered and the brown solid dried in vacuo to give 7-cyano-5H-thieno[3,2-c]pyridin-4-one (1.2 g, 78%). 1H NMR (DMSO): 8 ppm 7.56 (d, 1H, J=5.3 Hz), 7.80 (d, 1H, J=5.3 Hz), 8.36 (s, 1H), 12.34 (s, 1H). MS: m/z=175 (M-1).

References:

WO2005/105809,2005,A1 Location in patent:Page/Page column 28