Sodium Hydroxide → 2-(6-Formamidopyridin-2-yl)-2-ethoxyiminoacetic acid

HRID 2286655Notes

Reaction equation

HRID 2286655 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.[O:20]([NH2:23])[CH2:21][CH3:22]>C(O)C>[CH:3]([NH:5][C:6]1[N:11]=[C:10]([C:12](=[N:23][O:20][CH2:21][CH3:22])[C:13]([OH:15])=[O:14])[CH:9]=[CH:8][CH:7]=1)=[O:4]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 76850O-ethylhydroxylamine hydrochlorideHCID 13060174Ethyl 2-(6-formamidopyridin-2-yl)glyoxylate

Product 1

HCID 536595352-(6-Formamidopyridin-2-yl)-2-ethoxyiminoacetic acidYield 45.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1 N Sodium hydroxide solution (8.5 ml.) was added to a stirred solution of ethyl 2-(6-formamidopyridin-2-yl)-glyoxylate (1.9 g.) in ethanol (30 ml.) at room temperature and stirred at the same temperature for 30 minutes. After adding ethoxylamine hydrochloride (912 mg.) to the solution, the solution was stirred at room temperature for 4 hours. The resultant solution was concentrated under reduced pressure, and ethyl acetate and an aqueous solution of sodium bicarbonate were added to the residue. The aqueous layer was separated and ethyl acetate was added to the solution. The solution was adjusted to pH 1 with 10% hydrochloric acid. The ethyl acetate layer was separated, dried over magnesium sulfate and concentrated under reduced pressure. The residue was triturated with a mixture of diethyl ether and petroleum ether to give 2-(6-formamidopyridin-2-yl)-2-ethoxyiminoacetic acid (920 mg.), mp 155° to 156° C. (dec.).

Workup

  1. stirringthe solution was stirred at room temperature for 4 hours
  2. concentrationThe resultant solution was concentrated under reduced pressure, and ethyl acetate
  3. additionan aqueous solution of sodium bicarbonate were added to the residue
  4. customThe aqueous layer was separated
  5. additionethyl acetate was added to the solution
  6. customThe ethyl acetate layer was separated
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was triturated with a mixture of diethyl ether and petroleum ether

Sources & evidence

ORD record
ord-2c91bc77e7a74ae692ef997ba74ae1c2
Source dataset
uspto-grants-1981_05
Patent number
US04267176

Reaction notes

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