Reaction #41786

Reaction equation

MeCl2

5

4-amino-3-nitrophenol

6

[4-(4-amino-3-nitrophenoxy)(2-pyridyl)]-N-methylcarboxamide

sodium carbonate

→

desired product 7

nitroaniline

Solvents

DME H2O

water

ethyl acetate

Conditions

Workup

1. 1
   Otherby bubbling argon through the solution for 10 minutes
2. 2
   Otherthe reaction was sealed
3. 3
   TemperatureThe reaction was cooled to RT
4. 4
   OtherThe organic layer was separated from the aqueous layer
5. 5
   WashThe aqueous layer was washed once more with ethyl acetate
6. 6
   Dryingdried (Na2SO4)
7. 7
   Concentrationconcentrated under vacuum

Procedure

A solution of 5 (1 eq), 6 (1 eq), and sodium carbonate (1.2 eq) in DME/H2O (3:1) was degassed by bubbling argon through the solution for 10 minutes. Pd(II)(dppf)Cl2.MeCl2 (0.1 eq) was added to the reaction solution and the reaction was sealed. The reaction was heated at 100° C. overnight. The reaction was cooled to RT and ethyl acetate and water were added. The organic layer was separated from the aqueous layer. The aqueous layer was washed once more with ethyl acetate. The organic layers were combined, dried (Na2SO4), and concentrated under vacuum to yield the desired product 7. MS: MH+=469

Source