Ethanol → 3-Methoxy-5-nitropyridin-2-amine
Reaction equation
Cl[C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([N+:10]([O-:12])=[O:11])=[CH:4][N:3]=1.[OH-].[NH4+:14].C(O)C>C(OCC)(=O)C>[NH2:14][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([N+:10]([O-:12])=[O:11])=[CH:4][N:3]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
Into a 250 mL sealed tube were combined 2-chloro-3-methoxy-5-nitropyridine (0.50 g, 0.00265 mol), concentrated ammonium hydroxide (5 mL, 0.1 mol) and ethanol (20 mL). The mixture was heated to 80° C. and stirred overnight. After allowing to cool to room temperature, the mixture was reduced in vacuo and the residue was taken up in ethyl acetate (50 mL), then washed with equal amounts of brine and water (1×50 mL each). The organic layer was dried (Na2SO4), filtered and concentrated under vacuum to leave a solid (0.312 g, 69%) which was used directly in the next step without further purification. LC-MS 1.94 min. M/Z=171.0 (M+1).
Workup
- customInto a 250 mL sealed tube
- temperatureto cool to room temperature
- washwashed with equal amounts of brine and water (1×50 mL each)
- dry with materialThe organic layer was dried (Na2SO4)
- filtrationfiltered
- concentrationconcentrated under vacuum
Sources & evidence
- ORD record
- ord-4d3aaa966c2f48689d345d266f739549
- Source dataset
- uspto-grants-2007_12
- Patent number
- US07312233B2
Reaction notes
Loading…