Reaction #710590

Reaction equation

2,5,7-Trichloro-8-hydroxyquinoline

methylamine

→

5,7-Dichloro-2-methylamino-8-hydroxyquinoline

Solvents

ethanol

Conditions

Workup

1. 1
   Temperaturecooled
2. 2
   OtherThe precipitate was then isolated via filtration
3. 3
   Washwashed with diethyl ether

Procedure

2,5,7-Trichloro-8-hydroxyquinoline 10 (200 mg, 0.805 mmol) and a solution of methylamine in ethanol (12 mL of a 33% solution) were heated in a sealed vessel at 90° C. for 26 h, and cooled. The precipitate was then isolated via filtration and washed with diethyl ether. This provided pure 5,7-dichloro-2-methylamino-8-hydroxyquinoline (PBT 1047) as a pale yellow solid (186 mg, 95%). 1H NMR (DMSO-d6, 400 MHz): δ 8.80 (br, 1H), 7.98 (d, J=9.1, 1H), 7.48 (br, 1H), 7.25 (s, 1H), 6.90 (d, J=9.1, 1H), 2.98 (d, J=4.8, 3 H); mass spectrum: m/z 243, 245 (M++1, 100 and 66%, respectively).

Source