Triethylamine → 3'-(1-Methyl-3-nitro-2-oxo-1,2-dihydropyridin-4-ylamino)biphenyl-2-carbonitrile

4-Chloro-1-methyl-3-nitro-1H-pyridin-2-one (0.71 g, 3.8 mmol) and 3′-aminobiphenyl-2-carbonitrile (0.73 g, 3.8 mmol) were dissolved in triethylamine (5.25 ml, 37.8 mmol) and DMSO (5 ml) and heated at 90° C. for 18 h. The mixture was allowed to cool to ambient temperature then poured onto water (150 ml). The aqueous phase was extracted with ethyl acetate (2×150 ml), the combined organics were washed with water (3×75 ml) and brine (50 ml), dried over anhydrous sodium sulfate, filtered and evaporated to give a brown solid. The solid was triturated with diethyl ether (20 ml), filtered and left to air dry, to give 3′-(1-methyl-3-nitro-2-oxo-1,2-dihydropyridin-4-ylamino)biphenyl-2-carbonitrile (1.28 g, 98%) as a brown solid: δ (400 MHz, CDCl3) 3.50 (3H, s), 6.24 (1H, d, J 8), 7.26 (1H, d, J 8), 7.34 (1H, d, J 8), 7.48 (2H, dd, J 4 and 2), 7.51-7.59 (2H, m), 7.60 (1H, t, J 8), 7.68-7.72 (1H, m), 7.81 (1H, dd, J 8 and 1), 10.47 (1H, s).

1. additionthen poured onto water (150 ml)
2. extractionThe aqueous phase was extracted with ethyl acetate (2×150 ml)
3. washthe combined organics were washed with water (3×75 ml) and brine (50 ml)
4. dry with materialdried over anhydrous sodium sulfate
5. filtrationfiltered
6. customevaporated
7. customto give a brown solid
8. customThe solid was triturated with diethyl ether (20 ml)
9. filtrationfiltered
10. waitleft to air
11. customdry

ORD record

ord-6cc876ee4c09473ca654bf32563dc283

Source dataset

uspto-grants-2005_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06887885B2