Methane → Glycinamide

HRID 1975491Notes

Reaction equation

HRID 1975491 reaction equation
Cl.[NH2:2][CH2:3][C:4]([NH2:6])=[O:5].[OH-].[Na+].[F:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][C:11]=1[C:18]([CH:20]=O)=O.Cl.C>CO.C(Cl)Cl.CO>[NH2:2][CH2:3][C:4]([NH2:6])=[O:5].[F:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][C:11]=1[C:18]1[N:2]=[CH:3][C:4](=[O:5])[NH:6][CH:20]=1

Participants

9

Reactant 5

HCID 297MethaneHCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide2×HCID 2723639Glycinamide hydrochlorideHCID 19003558HCID 19003558, compound

Product 2

HCID 69020GlycinamideHCID 53820982HCID 53820982, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

An aqueous solution of glycinamide (0.027 mol, 3.03 g), which was prepared by neutralizing glycinamide hydrochloride with one equivalent of 10N NaOH, was slowly added to a stirring solution of 2-fluoro-5-methoxyphenyl glyoxal (0.027 mol, 5.42 g) in MeOH (35 mL) at 0° C. One equivalent of 10N NaOH (2.74 mL) was then added slowly to the resulting clear orange solution. After stirring overnight at room temperature the solution was acidified to pH~3 with 12N HCl and the methanol was evaporated under reduced pressure. The residue was partitioned between CH2Cl2 and water and the aqueous phase was extracted (5×) with CH2Cl2. The combined CH2Cl2 portions were dried (Na2SO4) and concentrated under reduced pressure to give a dark solid. The solid was dissolved in CH2Cl2 /MeOH, heated for five minutes with decolorizing charcoal and filtered through 2 inches of silica gel (5% MeOH/CH2Cl2 eluent). Evaporation of the solvents under reduced pressure afforded 5-(2-fluoro-5-methoxyphenyl)-pyrazin-2-one.

Workup

  1. customthe methanol was evaporated under reduced pressure
  2. customThe residue was partitioned between CH2Cl2 and water
  3. extractionthe aqueous phase was extracted (5×) with CH2Cl2
  4. dry with materialThe combined CH2Cl2 portions were dried (Na2SO4)
  5. concentrationconcentrated under reduced pressure
  6. customto give a dark solid
  7. filtrationfiltered through 2 inches of silica gel (5% MeOH/CH2Cl2 eluent)
  8. customEvaporation of the solvents under reduced pressure

Sources & evidence

ORD record
ord-91cf477bffcf470c862f381ef9fb621f
Source dataset
uspto-grants-1994_02
Patent number
US05286860

Reaction notes

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