Sodium Hydroxide → 2-(6-Formamidopyridin-2-yl)-2-methoxyiminoacetic acid
Reaction equation
[OH-].[Na+].[CH:3]([NH:5][C:6]1[N:11]=[C:10]([C:12](=O)[C:13]([O:15]CC)=[O:14])[CH:9]=[CH:8][CH:7]=1)=[O:4].Cl.[CH3:20][O:21][NH2:22]>C(O)C>[CH:3]([NH:5][C:6]1[N:11]=[C:10]([C:12](=[N:22][O:21][CH3:20])[C:13]([OH:15])=[O:14])[CH:9]=[CH:8][CH:7]=1)=[O:4]Participants
Procedure
2 N Sodium hydroxide solution [solvent:water (1 part)+ethanol (4 parts)] (14.87 ml.) was added to a solution of ethyl 2-(6-formamidopyridin-2-yl)glyoxylate (6.00 g.) in ethanol (180 ml.) at room temperature and stirred at the same temperature for 20 minutes. Methoxyamine hydrochloride (2.71 g.) was added to the resultant solution, stirred at room temperature for 1.5 hours and then concentrated to a small volume under reduced pressure. The precipitates were collected by filteration washed with ethyl acetate and water, dissolved in methanol and then treated with activated charcoal. The solution was concentrated under reduced pressure and then the precipitates were collected by filtration to give 2-(6-formamidopyridin-2-yl)-2-methoxyiminoacetic acid (3.63 g.), mp 170° to 171° C. (dec.).
Workup
- stirringstirred at room temperature for 1.5 hours
- concentrationconcentrated to a small volume under reduced pressure
- customThe precipitates were collected by filteration
- washwashed with ethyl acetate and water
- dissolutiondissolved in methanol
- additiontreated with activated charcoal
- concentrationThe solution was concentrated under reduced pressure
- filtrationthe precipitates were collected by filtration
Sources & evidence
- ORD record
- ord-59df2709aa214dc2b2f3b77ad5b7308c
- Source dataset
- uspto-grants-1981_05
- Patent number
- US04267176
Reaction notes
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