2,3-Dimethoxy-5-nitropyridine → 5,6-Dimethoxypyridin-3-amine
Reaction equation
[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][C:6]([N+:11]([O-])=O)=[CH:5][N:4]=1>[Pd].CCOC(C)=O>[CH3:10][O:9][C:8]1[CH:7]=[C:6]([NH2:11])[CH:5]=[N:4][C:3]=1[O:2][CH3:1]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 50 °C
Procedure
A stainless steel bomb was charged with 2,3-dimethoxy-5-nitropyridine (430 mg, 2335 μmol), 10% Pd/C (124 mg, 1168 μmol) and 4.7 mL EtOAc. The vessel was sealed and was purged with hydrogen once, before filling with hydrogen at a pressure of 2 atm. The reaction mixture was heated at 50° C. for 3 h. Upon cooling, the mixture was filtered through a pad of Celite, rinsing with EtOAc. The filtrate was concentrated and passed through a silica plug using 5% MeOH/DCM. The filtrate was concentrated to provide 5,6-dimethoxypyridin-3-amine as a peach colored oil that crystallized upon standing. GC/MS confirmed the correct mass to be [M+H]=155.
Workup
- customThe vessel was sealed
- customwas purged with hydrogen once
- temperatureUpon cooling
- filtrationthe mixture was filtered through a pad of Celite
- washrinsing with EtOAc
- concentrationThe filtrate was concentrated
- concentrationThe filtrate was concentrated
Sources & evidence
- ORD record
- ord-14abc0a7f44b48bca11b5be4b87175fe
- Source dataset
- uspto-grants-2013_10
- Patent number
- US08557816B2
Reaction notes
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