Reaction #710597

Reaction equation

isopropyl ether

7-chloro-5-(pyridin-3-yl)-8-isopropoxyquinoline

boron trichloride

→

7-chloro-5-(pyridin-3-yl)-quinolin-8-ol

Yield 94.6%

Conditions

Procedure

Cleavage of the isopropyl ether 22 (20 mg, 0.07 mmol) with boron trichloride following the method outlined in Example 8, gave 7-chloro-5-(pyridin-3-yl)-quinolin-8-ol (PBT 1057) as a pale straw-coloured solid (17 mg, 94%). 1H NMR (CD3OD, 400 MHz): δ 9.16 (m, 2H), 9.04 (d, J=5.8, 1H), 8.93 (dd, J=1.2 and 8.6, 1 H), 8.84 (m, 1H), 8.30 (dd, J=5.8 and 8.1, 1H), 8.09 (s, 1H), 8.08 (dd, J=5.1 and 8.6, 1H).

Source