Sodium Hydroxide → HCID 54045511, compound

HRID 2286657Notes

Reaction equation

HRID 2286657 reaction equation
C(NC1C=CN=C(C(=O)C(SC)=O)C=1)=O.[OH-].[Na+].[CH:18]([NH:20][C:21]1[CH:26]=[CH:25][N:24]=[C:23]([C:27](=O)[C:28]([OH:30])=[O:29])[CH:22]=1)=[O:19].Cl.[CH3:33][O:34][NH2:35]>CO>[CH:18]([NH:20][C:21]1[CH:26]=[CH:25][N:24]=[C:23]([C:27](=[N:35][O:34][CH3:33])[C:28]([OH:30])=[O:29])[CH:22]=1)=[O:19]

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 521874O-Methylhydroxylamine hydrochlorideHCID 13060229HCID 13060229, compoundHCID 23316861HCID 23316861, compound

Product 1

HCID 54045511HCID 54045511, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of S-methyl 2-(4-formamidopyridin-2-yl)thioglyoxylate (1.07 g.), methanol (20 ml.) and 1 N aqueous solution of sodium hydroxide (5.7 ml.) was stirred for 50 minutes at ambient temperature to give a solutions containing 2-(4-formamidopyridin-2-yl)glyoxylic acid. To the solution was added O-methylhydroxylamine hydrochloride (438 mg.), and the mixture was stirred for an hour at ambient temperature. After the removal of the solvent from the reaction mixture, to the residue was added water (5 ml.), and the mixture was washed with ethyl acetate and then water was distilled off. The remaining water in the residue was azeotropically removed with ethanol and benzene in turn to give a pale brown powder of 2-(4-formamidopyridin-2-yl)-2-methoxyiminoacetic acid (syn isomer) (960 mg.).

Workup

  1. customto give a solutions
  2. stirringthe mixture was stirred for an hour at ambient temperature
  3. customAfter the removal of the solvent from the reaction mixture
  4. additionto the residue was added water (5 ml.)
  5. washthe mixture was washed with ethyl acetate
  6. distillationwater was distilled off
  7. customThe remaining water in the residue was azeotropically removed with ethanol and benzene in turn

Sources & evidence

ORD record
ord-f6e4d95294ad4e919f7c2a83ae24a203
Source dataset
uspto-grants-1981_05
Patent number
US04267176

Reaction notes

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