N,N-dimethyl-5-nitropyridin-2-amine → N2,N2-dimethylpyridine-2,5-diamine
Reaction equation
[CH3:1][N:2]([CH3:12])[C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-])=O)=[CH:5][N:4]=1.C([O-])(O)=O.[Na+]>CCO>[NH2:9][C:6]1[CH:5]=[N:4][C:3]([N:2]([CH3:12])[CH3:1])=[CH:8][CH:7]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
A stirred mixture of the product from Step 1 (7.70 g, 0.0461 mol) and stannous chloride dihydrate (56.4 g, 0.250 mol) in absolute EtOH (100 ml) was warmed to 80° C. during 15 minutes and kept at that temperature for 35 minutes. The resulting mixture was kept at ambient temperature for 1 hour, poured onto ice (400 ml) and mixed with NaHCO3 (15 g). It was adjusted to a pH of 8-9 with saturated aqueous NaHCO3 and extracted with EtOAc; the extract was washed with water and brine dried (MgSO4) and concentrated to give 5.98 g of crude product. Pan of this was purified by silica gel chromatography, with 5% MeOH--0.25% NH4OH--CHCl3 to give the titled product.
Workup
- waitThe resulting mixture was kept at ambient temperature for 1 hour
- additionpoured onto ice (400 ml)
- extractionextracted with EtOAc
- washthe extract was washed with water and brine
- dry with materialdried (MgSO4)
- concentrationconcentrated
- customto give 5.98 g of crude product
- customPan of this was purified by silica gel chromatography, with 5% MeOH--0.25% NH4OH--CHCl3
Sources & evidence
- ORD record
- ord-0a0be0aa42e24f23ab9f3191a0462d13
- Source dataset
- uspto-grants-1996_10
- Patent number
- US05567722
Reaction notes
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