Hydrochloric Acid → (E)-3-(6-Amino4-methylpyridin-3-yl)acrylic acid HCl salt
Reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]([O:12]CC)=[O:11])=[C:4]([CH3:15])[CH:3]=1.[ClH:16]>CC(O)=O>[ClH:16].[NH2:1][C:2]1[N:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]([OH:12])=[O:11])=[C:4]([CH3:15])[CH:3]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
To ethyl (E)-3-(6-amino-4-methylpyridin-3-yl)acrylate (1.50 g, 7.3 mmole) was added HOAc (15 mL) and conc. HCl (15 mL). The solution was stirred at 100° C. for 10 hr, cooled to RT, and concentrated to dryness. Trituration with Et2O, filtration and drying under vacuum gave the title compound (1.65 g, quantitative) as a white solid: LCMS (ES) m/e 179.2 (M+H)+; 1H NMR (400 MHz, DMSO-d6) δ 8.37 (s, 1 H), 8.28 (br s, 3 H), 7.51 (d, J=16.0 Hz, 1 H), 6.86 (s, 1 H), 6.46 (d, J=16.0 Hz, 1 H), 2.41 (s, 3 H).