2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 2-(6-Methoxypyridin-3-yl)-1,3-benzoxazol-6-ol
Reaction equation
[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([CH:9]=[N:10][C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][C:12]=2[OH:18])=[CH:5][CH:4]=1.C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N>C(Cl)Cl>[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([C:9]2[O:18][C:12]3[CH:13]=[C:14]([OH:17])[CH:15]=[CH:16][C:11]=3[N:10]=2)=[CH:5][CH:4]=1Participants
4
Procedure
4-{[(6-methoxypyridin-3-yl)methylene]amino}benzene-1,3-diol was dissolved in CH2Cl2 (30 mL) and DDQ was added. The reaction mixture was stirred over night at r.t., SiO2 was added and the solvents were removed under reduced pressure. The crude product was purified by flash column chromatography to give the title compound (189.1 mg). 1H NMR δ ppm 9.88 (s, 1H) 8.90 (dd, 1H) 8.35 (dd, 1H) 7.56 (d, 1H) 7.09 (d, 1H) 6.85 (dd, 1H) 3.95 (s, 3H); MS m/z 243 (M+H).