Reaction #1806

Reaction equation

6-methoxytetralone

4-hydroxyaniline

→

6-Methoxy-1-[(4-hydroxy)phenyl]imino-1,2,3,4-tetrahydronaphthalene

Conditions

Workup

1. 1
   TemperatureAfter cooling to ambient temperature
2. 2
   Otherthe solid mass was recrystallized from toluene/methanol

Procedure

A mixture of 6-methoxytetralone (25 g, 142 mmol) and 4-hydroxyaniline (16.3 g, 149 mmol) was heated to 180° C. under a nitrogen stream for 2 h. After cooling to ambient temperature, the solid mass was recrystallized from toluene/methanol: 1H NMR (300 MHz) d 8.15 (d, J=9.7 Hz, 1H), 6.5-7.9 (m, 6H), 3.80 (s, 3H), 2.84 (t, J=7.3 Hz, 2H), 2.51 (t, J=6.8 Hz, 2H), 1.85 (m, 2H).

Source