Reaction #2329004

Reaction equation

4-{[(6-methoxypyridin-3-yl)methylene]amino}benzene-1,3-diol

DDQ

→

title compound

2-(6-Methoxypyridin-3-yl)-1,3-benzoxazol-6-ol

Solvents

CH2Cl2

Conditions

Workup

1. 1
   workup.ADDITIONSiO2 was added
2. 2
   Otherthe solvents were removed under reduced pressure
3. 3
   OtherThe crude product was purified by flash column chromatography

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).

Source