Methanol → HCID 54218915, compound

HRID 2286660Notes

Reaction equation

HRID 2286660 reaction equation
[CH:1]([NH:3][C:4]1[N:9]=[CH:8][C:7](C(=O)C(SC)=O)=[CH:6][CH:5]=1)=[O:2].[OH-].[Na+].Cl.[CH3:19][O:20][NH2:21].[C:22](=[O:25])(O)[O-:23].[Na+].[CH3:27]O>O>[CH:1]([NH:3][C:4]1[C:5]([C:27](=[N:21][O:20][CH3:19])[C:22]([OH:23])=[O:25])=[CH:6][CH:7]=[CH:8][N:9]=1)=[O:2]

Participants

7

Reactant 5

HCID 887MethanolHCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 521874O-Methylhydroxylamine hydrochlorideHCID 13060228HCID 13060228, compound

Product 1

HCID 54218915HCID 54218915, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of S-methyl 2-(6-formamidopyridin-3-yl)thioglyoxylate (13 g.), methanol (50 ml.), 1 N aqueous solution of sodium hydroxide (58 ml.) and water (150 ml.) was stirred at ambient temperature for 30 minutes. To the mixture was added O-methylhydroxylamine hydrochloride (4.85 g.) and then stirred for an hour. The reaction mixture was adjusted to pH 7 with an aqueous solution of sodium bicarbonate, and the methanol was removed by distillation under reduced pressure. The remaining aqueous solution was washed with ethyl acetate and thereto was added ethyl acetate. The resultant mixture was adjusted to pH 2 with 10% hydrochloric acid and thereto was added sodium chloride, and the mixture was stirred for a while. The precipitates were collected by filtration washed with diisopropyl ether and then dried to give 2-(2-formamidopyridin-3-yl)-2-methoxyiminoacetic acid (syn isomer) (2.0 g.), mp. 159° to 161° C. (dec.).

Workup

  1. stirringstirred for an hour
  2. customthe methanol was removed by distillation under reduced pressure
  3. washThe remaining aqueous solution was washed with ethyl acetate
  4. additionwas added ethyl acetate
  5. additionwas added sodium chloride
  6. stirringthe mixture was stirred for a while
  7. filtrationThe precipitates were collected by filtration
  8. washwashed with diisopropyl ether
  9. customdried

Sources & evidence

ORD record
ord-33f607151af5424c9149f997d324e14d
Source dataset
uspto-grants-1981_05
Patent number
US04267176

Reaction notes

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