Tert-butyl 4-[4-(methylamino)-3-nitrophenoxy]pyridine-2-carboxylate → Tert-butyl4-[3-amino-4-(methylamino)phenoxy]pyridine-2-carboxylate

HRID 13447Notes

Reaction equation

HRID 13447 reaction equation
[CH3:1][NH:2][C:3]1[CH:22]=[CH:21][C:6]([O:7][C:8]2[CH:13]=[CH:12][N:11]=[C:10]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH:9]=2)=[CH:5][C:4]=1[N+:23]([O-])=O>[Pd].CO>[NH2:23][C:4]1[CH:5]=[C:6]([CH:21]=[CH:22][C:3]=1[NH:2][CH3:1])[O:7][C:8]1[CH:13]=[CH:12][N:11]=[C:10]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH:9]=1

Participants

4

Reactant 1

HCID 22040453Tert-butyl 4-[4-(methylamino)-3-nitrophenoxy]pyridine-2-carboxylate

Product 1

HCID 22040526Tert-butyl4-[3-amino-4-(methylamino)phenoxy]pyridine-2-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

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.

Workup

  1. customflushed with nitrogen
  2. customHydrogen was flushed through the reaction for 1-2 hours or until the reaction
  3. customNitrogen was flushed through the reaction for 15 minutes before the reaction
  4. filtrationwas filtered through a celite pad
  5. washThe celite pad was washed with excess methanol
  6. concentrationfollowed by concentration under reduced pressure

Sources & evidence

ORD record
ord-d53596ef137247da833ff0cac6ec958a
Source dataset
uspto-grants-2010_06
Patent number
US07728010B2

Reaction notes

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