Thionyl Chloride → HCID 22030137, compound
Reaction equation
[N+:1]([C:4]1[C:9](=O)[NH:8][CH:7]=[C:6]([C:11]2[C:16]([C:17]([F:20])([F:19])[F:18])=[CH:15][CH:14]=[CH:13][N:12]=2)[CH:5]=1)([O-:3])=[O:2].S(Cl)([Cl:23])=O>CN(C=O)C>[Cl:23][C:9]1[N:8]=[CH:7][C:6]([C:11]2[C:16]([C:17]([F:20])([F:19])[F:18])=[CH:15][CH:14]=[CH:13][N:12]=2)=[CH:5][C:4]=1[N+:1]([O-:3])=[O:2]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Heat a solution of 5′-nitro-3-trifluoromethyl-1′H[2,3′]bipyridinyl-6′-one (25 g, 0.088 mol), thionyl chloride (300 mL) and DMF (3 mL) to reflux for 4 hours. Remove the volatiles by rotary evaporation and partition the residue between ethyl acetate (350 mL) and saturated sodium bicarbonate solution (250 mL). Extract the aqueous layer with further ethyl acetate (250 mL) and wash the combined organics with brine (250 mL). Dry (MgSO4) and concentrate under reduced pressure to give the title compound (25 g, 93%) as a yellow oil.