Reaction #367192

Reaction equation

sodium

7-chloro-8-nitroquinoline

methanol

→

7-Methoxy-8-nitroquinoline

Conditions

Workup

1. 1
   TemperatureThis mixture was refluxed for 3 hr
2. 2
   Temperaturecooled
3. 3
   Filtrationfiltered
4. 4
   Otherto collect the precipitated solid
5. 5
   Othercollected on
6. 6
   Filtrationa filter
7. 7
   Otherdried
8. 8
   Otheryield
9. 9
   Otherafter recrystallization from toluene, 16.12 g (88%)

Procedure

To a freshly prepared solution of sodium (16.5 g, 0.720 mol) in methanol (750 mL) was added 7-chloro-8-nitroquinoline (18.72 g, 0.090 mol) [E. Fourneau, M. and Mme. Trefouel, and A. Wancolle, Bull. Soc. Chim. Fr., 47, 738(1930); A. K. Sen, N. K. Ray, V. P. Basu, J. Sci. Ind. Res., 11B, 322(1952) (C.A. 47, 4339e)]. This mixture was refluxed for 3 hr, cooled, then filtered to collect the precipitated solid. This solid was slurried in water, collected on a filter and dried; yield, after recrystallization from toluene, 16.12 g (88%); mp 178°-178.5°: Anal. Calcd for C10H8N2O3 : C, 58.82; H, 3.95; N, 13.72. Found: C, 58.66; H, 3.78; N, 13.69.

Source