Reaction #172402

Reaction equation

hydrochloric acid

potassium tert-butoxide

3-methoxypyridin-2(1H)-one

1-fluoro-2-methyl-4-nitrobenzene

→

3-Methoxy-1-(2-methyl-4-nitrophenyl)pyridin-2(1H)-one

Solvents

water

dimethyl sulphoxide

Conditions

Workup

1. 1
   Temperaturethe reaction solution is heated at 80° C. for 20 h
2. 2
   ExtractionThe solution is extracted repeatedly with dichloromethane
3. 3
   WashThe combined organic extracts are washed with water and saturated sodium chloride solution
4. 4
   Dryingdried over sodium sulphate
5. 5
   Filtrationfiltered
6. 6
   Otherevaporated under reduced pressure
7. 7
   OtherThe solid obtained
8. 8
   Washis washed with a little tert-butyl methyl ether
9. 9
   Filtrationfiltered off
10. 10
    Otherdried under reduced pressure

Procedure

28.5 g (228 mol) of 3-methoxypyridin-2(1H)-one are dissolved in 850 ml of dimethyl sulphoxide, and 31 g (273 mmol) of potassium tert-butoxide are added at RT. The suspension is stirred at RT for 30 min, and 35 g (228 mmol) of 1-fluoro-2-methyl-4-nitrobenzene are then added, and the reaction solution is heated at 80° C. for 20 h. The solution is then carefully diluted with 1 l of water and adjusted to pH 1-2 using 1N hydrochloric acid. The solution is extracted repeatedly with dichloromethane. The combined organic extracts are washed with water and saturated sodium chloride solution, dried over sodium sulphate, filtered and evaporated under reduced pressure. The solid obtained is washed with a little tert-butyl methyl ether, filtered off and dried under reduced pressure. This gives 42.8 g (72% of theory) of the desired compound.

Source