Pyridine, 2,5-dimethyl-4-nitro-, 1-oxide → 2,5-dimethylpyridin-4-amine
Reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[C:5]([CH3:11])=[CH:4][N+:3]=1[O-]>C(O)(=O)C.[Pd]>[CH3:1][C:2]1[CH:7]=[C:6]([NH2:8])[C:5]([CH3:11])=[CH:4][N:3]=1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 60 °C
Procedure
A mixture of 2,5-dimethyl-4-nitropyridine N-oxide (7.0 g, 41.7 mmol) and 10% Pd/C (1.2 g) in acetic acid (60 mL) was stirred under hydrogen at 60° C. for 18 h. The solution was cooled, filtered, and diluted with water (100 mL). The aqueous mixture was neutralized with solid sodium carbonate. The solution was extracted with DCM (250 mL×5), and the combined organic phase was dried with anhydrous sodium sulfate and concentrated to give 4.6 g of the product as a yellow solid. MS (ESI): m/z 123.1 [M+H]+.
Workup
- temperatureThe solution was cooled
- filtrationfiltered
- additiondiluted with water (100 mL)
- extractionThe solution was extracted with DCM (250 mL×5)
- dry with materialthe combined organic phase was dried with anhydrous sodium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-a90349c0c8dd4ca88a7452905bd82b4a
- Source dataset
- uspto-grants-2015_03
- Patent number
- US08969349B2
Reaction notes
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