4-(4-Methylamino-3-nitro-phenoxy)-pyridine-2-carboxylic acid (2-hydroxy-ethyl)-amide → 4-(3-Amino-4-methylamino-phenoxy)-pyridine-2-carboxylic acid (2-hydroxy-ethyl)-amide
Reaction equation
[OH:1][CH2:2][CH2:3][NH:4][C:5]([C:7]1[CH:12]=[C:11]([O:13][C:14]2[CH:19]=[CH:18][C:17]([NH:20][CH3:21])=[C:16]([N+:22]([O-])=O)[CH:15]=2)[CH:10]=[CH:9][N:8]=1)=[O:6]>[Pd].CO>[OH:1][CH2:2][CH2:3][NH:4][C:5]([C:7]1[CH:12]=[C:11]([O:13][C:14]2[CH:19]=[CH:18][C:17]([NH:20][CH3:21])=[C:16]([NH2:22])[CH:15]=2)[CH:10]=[CH:9][N:8]=1)=[O:6]Participants
4
Procedure
A solution of 4-(4-methylamino-3-nitro-phenoxy)-pyridine-2-carboxylic acid (2-hydroxy-ethyl)-amide (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 before it was all removed by evaporation under reduced pressure to afford the product as a light yellow solid. LCMS m/z 303.2 (MH+), tR=1.5 min.
Workup
- customflushed with nitrogen
- customHydrogen was flushed through the reaction for 1-2 hours or until the reaction
- customNitrogen was flushed through the reaction for 15 minutes before the reaction
- filtrationwas filtered through a celite pad
- washThe celite pad was washed with excess methanol before it
- customall removed by evaporation under reduced pressure
Sources & evidence
- ORD record
- ord-a12b36bfb55e4c5faaa99547c976eee3
- Source dataset
- uspto-grants-2012_10
- Patent number
- US08299108B2
Reaction notes
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