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| Typical applications of Bredereck's reagent（CAS:5815-08-7）（6） |
| 2022-06-19 |
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2-[1-(2,5-dimethylpyrrol)]-pyridylacetonitrile
A mixture of 3.0 g of 2-[1-(2,4-dimethylpyrrolyl)]-4-methylpyridine and
8.3 g of t-butoxybisdimethylaminomethane was stirred at 110°C for 4 hours.
The reaction solution was cooled and from which the t-butoxybisdimethylaminomethane was distilled off under reduced pressure, to obtain blackish brown, oily residue.
Ten (10) mL of water and 4.6 g of hydroxylamine-O-sulfonic acid were added to the residue and stirred at room temperature for an hour.
The reaction solution was rendered basic by addition of saturated aqueous sodium hydrogencarbonate solution under cooling with ice, and extracted with methylene chloride.
The methylene chloride extract was dried over anhydrous magnesium sulfate and from which the solvent was distilled off under reduced pressure.
The resultant residue was purified on 100 g silica gel column chromatography
(eluent, chloroform: methanol = 100 : 1) to provide 2.8 g (yield: 82%) of the title compound as pale yellow crystal.
1H-NMR(CDCl3)δ:8.62(d,J=5.1Hz,1H),7.40-7.20(m,2H), 5.91(s,2H),3.84(s,2H),2.13(s,6H)
Ref : EP2036905, 2009, A1
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