N-[3-tert-butyl-2-methoxy-5-(2-methoxypyridin-3-yl)phenyl]-4-nitrobenzamide → 4-amino-N-[3-tert-butyl-2-methoxy-5-(2-methoxypyridin-3-yl)phenyl]benzamide

HRID 2390821Notes

Reaction equation

HRID 2390821 reaction equation
[C:1]([C:5]1[C:6]([O:31][CH3:32])=[C:7]([NH:19][C:20](=[O:30])[C:21]2[CH:26]=[CH:25][C:24]([N+:27]([O-])=O)=[CH:23][CH:22]=2)[CH:8]=[C:9]([C:11]2[C:12]([O:17][CH3:18])=[N:13][CH:14]=[CH:15][CH:16]=2)[CH:10]=1)([CH3:4])([CH3:3])[CH3:2]>CCOC(C)=O.CO.[Pd]>[NH2:27][C:24]1[CH:25]=[CH:26][C:21]([C:20]([NH:19][C:7]2[CH:8]=[C:9]([C:11]3[C:12]([O:17][CH3:18])=[N:13][CH:14]=[CH:15][CH:16]=3)[CH:10]=[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[C:6]=2[O:31][CH3:32])=[O:30])=[CH:22][CH:23]=1

Participants

4

Reactant 1

HCID 67069874N-[3-tert-butyl-2-methoxy-5-(2-methoxypyridin-3-yl)phenyl]-4-nitrobenzamide

Product 1

HCID 670700384-amino-N-[3-tert-butyl-2-methoxy-5-(2-methoxypyridin-3-yl)phenyl]benzamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

step 4—To a solution of 102 (0.36 g, 0.82 mmol) in EtOAc/MeOH (2:1, 15 mL) was added 10% Pd/C (0.035 g). A stream of hydrogen gas was bubbled through the solution for 20 min, and the white solid precipitate that formed was recovered by filtration to afford 4-amino-N-[3-tert-butyl-2-methoxy-5-(2-methoxypyridin-3-yl)phenyl]benzamide (104).

Workup

  1. customA stream of hydrogen gas was bubbled through the solution for 20 min
  2. customthe white solid precipitate that formed
  3. filtrationwas recovered by filtration

Sources & evidence

ORD record
ord-60a835d39838461a8ac2700fbb7d9f6a
Source dataset
uspto-grants-2012_09
Patent number
US08273773B2

Reaction notes

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