2-(2,4-dimethoxyphenyl)pyridine → HCID 135433735, compound
Reaction equation
C[O:2][C:3]1[CH:8]=[C:7]([O:9]C)[CH:6]=[CH:5][C:4]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=1>Cl.N1C=CC=CC=1.ClCCl>[OH:2][C:3]1[CH:8]=[C:7]([OH:9])[CH:6]=[CH:5][C:4]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 160 °C
Procedure
A mixture of 2-(2,4-dimethoxyphenyl)pyridine (14 g) in pyridine hydrochloride (121 g) is heated to 160° C. and the resulting melt is heated at 160° C. for 7 hours. The mixture is then cooled, diluted with dichloromethane, washed with hydrochloric acid (2 M) and water, dried and evaporated. The residual oil is subjected to flash chromatography on silica gel, eluting with a mixture of pentane and ethyl acetate (1:1 v/v), to give 2-(2,4-dihydroxyphenyl)pyridine (8.0 g) in the form of a solid, m.p. 170-172° C. [NMR(CDCl3):- 6.3(1H,s),6.4(1H,d),7.3(1H,m), 7.8(1H,d),7.9(1H,t),8.0(1H,d),8.5(1H,d).