Ammonia → HCID 178513810, compound

HRID 392371Notes

Reaction equation

HRID 392371 reaction equation
[F:1][C:2]1[N:7]=[C:6]([C:8](OC)=[O:9])[C:5](=[O:12])[NH:4][CH:3]=1.[NH3:13].C(OCC)(=O)C.C(=O)([O-])O.[Na+]>CO.O>[F:1][C:2]1[N:7]=[C:6]([C:8]([NH2:13])=[O:9])[C:5]([OH:12])=[N:4][CH:3]=1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 22662805HCID 22662805, compound

Product 1

HCID 178513810HCID 178513810, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

In 3.0 mL of methanol was dissolved 0.12 g of methyl 6-fluoro-3-oxo-3,4-dihydro-2-pyrazinecarboxylate. Then, gaseous ammonia was introduced into the solution at an ice-cooled temperature for a period of 10 minutes, after which the mixture thus obtained was allowed to stand at room temperature for 2 days. The solvent was removed under reduced pressure, the residue thus obtained was added to a mixture of 30 mL of ethyl acetate and 30 ml of water, pH was adjusted to 7.5 with saturated aqueous solution of sodium hydrogen carbonate, and the organic layer was separated. After adding 30 mL of ethyl acetate to the remaining aqueous layer, pH was adjusted to 1.0 with 1 mol/L hydrochloric acid, and the whole mixture was extracted with two 15 mL portions of ethyl acetate. The organic layers thus obtained were united, washed successively with 15 mL of water and 15 mL of saturated aqueous solution of sodium chloride and dried on anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The solid product thus obtained was washed with diisopropyl ether to obtain 0.015 g of 6-fluoro-3-hydroxy-2-pyrazinecarboxamide as a yellow-colored solid product.

Workup

  1. temperaturecooled temperature for a period of 10 minutes
  2. customafter which the mixture thus obtained
  3. customThe solvent was removed under reduced pressure
  4. customthe residue thus obtained
  5. customthe organic layer was separated
  6. additionAfter adding 30 mL of ethyl acetate to the remaining aqueous layer, pH
  7. extractionthe whole mixture was extracted with two 15 mL portions of ethyl acetate
  8. customThe organic layers thus obtained
  9. washwashed successively with 15 mL of water and 15 mL of saturated aqueous solution of sodium chloride
  10. dry with materialdried on anhydrous magnesium sulfate
  11. customthe solvent was removed under reduced pressure
  12. customThe solid product thus obtained
  13. washwas washed with diisopropyl ether

Sources & evidence

ORD record
ord-3b8eb7ff3c6d447cb1bde78e50816186
Source dataset
uspto-grants-2004_10
Patent number
US06800629B2

Reaction notes

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