Hydrochloric Acid → Ethyl 2-chloro-4-methylnicotinate
Reaction equation
[ClH:1].C([C:4](=[C:10]([CH3:16])[CH:11]=[CH:12][N:13](C)[CH3:14])[C:5]([O:7][CH2:8][CH3:9])=[O:6])#N>C(O)C>[Cl:1][C:14]1[N:13]=[CH:12][CH:11]=[C:10]([CH3:16])[C:4]=1[C:5]([O:7][CH2:8][CH3:9])=[O:6]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Hydrogen chloride was introduced to a stirred mixture of 164 g (0.839 mole) of crude ethyl 2-cyano-5-(N,N-dimethylamino)-3-methyl-2,4-pentadienoate (5) in 500 mL ethanol at 20-45° C. The mixture was stirred at ambient temperature overnight, then heated to reflux for 8 hours. The ethanol was removed under reduced pressure and the residue distilled under high vacuum at 84-94° C., to give 47.7 g (30.4%) of a yellow oil, MH+ 200, NMR (CDCl3), ppm: 1.42 (t,3H); 2.36 (s,3H); 4.46 (q,2H); 7.12 (d,lH); 8.28 (d,1H).