Potassium Hydroxide → 3-Hydrazinyl-2-methoxypyridine
Reaction equation
[NH2:1][C:2]1[C:3]([O:8][CH3:9])=[N:4][CH:5]=[CH:6][CH:7]=1.[N:10]([O-])=O.[Na+].O.O.Cl[Sn]Cl.[OH-].[K+]>Cl.O>[NH:1]([C:2]1[C:3]([O:8][CH3:9])=[N:4][CH:5]=[CH:6][CH:7]=1)[NH2:10]Participants
7
Conditions
- Temperature
- 0 °C
Procedure
To a stirred solution of 3-amino-2-methoxypyridine (5 g, 40.3 mmol) in 6N HCl (80 mL) was added dropwise a solution of NaNO2 (2.78 g, 40.3 mmol) in water (50 mL) at 0° C. After 30 min at this temperature, a solution of SnCl2.2H2O (22.72 g, 101 mmol) in 6N HCl (80 mL) was added dropwise at 0° C. The reaction mixture was stirred 90 min at 0° C. The reaction mixture was adjusted to pH˜10-11 with a solution of KOH 40% in water and extracted with EtOAc. The combined organic layers were washed with water, dried over Na2SO4 and evaporated under reduced pressure to afford the title product (4.97 g, 33.9 mmol, 84% yield) as red oil. tR: 0.31 min (LC-MS 2); ESI-MS: 140 [M+H]+ (LC-MS 2).
Workup
- extractionextracted with EtOAc
- washThe combined organic layers were washed with water
- dry with materialdried over Na2SO4
- customevaporated under reduced pressure
Sources & evidence
- ORD record
- ord-05699739ba3b498cb68c4d9712ebcf80
- Source dataset
- uspto-grants-2015_03
- Patent number
- US08975417B2
Reaction notes
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