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

HRID 2286651Notes

Reaction equation

HRID 2286651 reaction equation
[OH-:1].[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.[NH2:20]O>C(O)C>[CH:3]([NH:5][C:6]1[N:11]=[C:10]([C:12](=[N:20][OH:1])[C:13]([OH:15])=[O:14])[CH:9]=[CH:8][CH:7]=1)=[O:4]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 13060174Ethyl 2-(6-formamidopyridin-2-yl)glyoxylate

Product 1

HCID 1363356462-(6-Formamidopyridin-2-yl)-2-hydroxyiminoacetic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1 N Sodium hydroxide (27.5 ml.) was added to a stirred solution of ethyl 2-(6-formamidopyridin-2-yl)-glyoxylate (5.55 g.) in ethanol (100 ml.) at room temperature, and the solution was stirred at the same temperature for 30 minutes. To the solution was added hydroxylamine hydrochloride (1.9 g.) all at once, and the solution was stirred at room temperature for 2 hours. After removing ethanol from the resultant solution under reduced pressure, ethylacetate was added to the residue, and then the solution was adjusted to pH 7 with an aqueous solution of sodium bicarbonate. The aqueous layer was separated and adjusted to pH 2 with 10% hydrochloric acid. The precipitates were collected by filtration, washed with water and dried to give 2-(6-formamidopyridin-2-yl)-2-hydroxyiminoacetic acid (3.6 g.), mp 190° to 192° C. (dec.).

Workup

  1. stirringwas stirred at room temperature for 2 hours
  2. customAfter removing ethanol from the resultant solution under reduced pressure, ethylacetate
  3. additionwas added to the residue
  4. customThe aqueous layer was separated
  5. filtrationThe precipitates were collected by filtration
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-668558a4a0a4481fa21e35e2351cb4bc
Source dataset
uspto-grants-1981_05
Patent number
US04267176

Reaction notes

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