2-Amino-6-methoxy-3-nitropyridine → 2,3-Diamino-6-methoxypyridine
Reaction equation
[NH2:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][CH:5]=[C:4]([O:11][CH3:12])[N:3]=1>CO.C(O)C>[NH2:1][C:2]1[C:7]([NH2:8])=[CH:6][CH:5]=[C:4]([O:11][CH3:12])[N:3]=1Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
2-Amino-6-methoxy-3-nitropyridine (2.8 g, 16.5 mmol) was dissolved in warm 1:1 methanol/ethanol (200 mL). The solution was cooled, purged with argon, and 10% palladium on carbon was added (0.45 g). Hydrogen was introduced (1 atm) and the reaction stirred until complete. The catalyst was filtered and the solvent evaporated from the filtrate to give the title compound. MS 140 (M+1) 1H NMR (500 MHz, CDCl3) δ 6.93 (d, J=8 Hz, 1H), 6.04 (d, J=8 Hz, 1H), 4.15 (br s, 2H), 3.80 (s, 3H), 3.0 (br s, 2H).
Workup
- temperatureThe solution was cooled
- custompurged with argon, and 10% palladium on carbon
- additionwas added (0.45 g)
- additionHydrogen was introduced (1 atm)
- filtrationThe catalyst was filtered
- customthe solvent evaporated from the filtrate
Sources & evidence
- ORD record
- ord-c9e79d9f53704fd4b417074d6b19b17e
- Source dataset
- uspto-grants-2009_05
- Patent number
- US07534784B2
Reaction notes
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