Reaction #41725

Reaction equation

tert-butyl 4-[4-(methylamino)-3-nitrophenoxy]pyridine-2-carboxylate

→

product

tert-butyl 4-[3-amino-4-(methylamino)phenoxy]pyridine-2-carboxylate

Solvents

methanol

Conditions

Workup

1. 1
   Otherflushed with nitrogen
2. 2
   OtherHydrogen was flushed through the reaction for 1-2 hours or until the reaction
3. 3
   OtherNitrogen was flushed through the reaction for 15 minutes before the reaction
4. 4
   Filtrationwas filtered through a celite pad
5. 5
   WashThe celite pad was washed with excess methanol
6. 6
   Concentrationfollowed by concentration under reduced pressure

Procedure

A solution of tert-butyl 4-[4-(methylamino)-3-nitrophenoxy]pyridine-2-carboxylate (1 eq) and 10% palladium on carbon (0.1 eq) in methanol was stirred at room temperature and flushed with nitrogen. Hydrogen was flushed through the reaction for 1-2 hours or until the reaction was determined to be complete by HPLC. Nitrogen was flushed through the reaction for 15 minutes before the reaction was filtered through a celite pad. The celite pad was washed with excess methanol followed by concentration under reduced pressure to afford the product as a light yellow solid. MS: MH+=316.

Source