Oxalic Acid → HCID 23047488, compound

HRID 2107073Notes

Reaction equation

HRID 2107073 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][C:5]([C:8](=[N:10][OH:11])[NH2:9])=[CH:4][CH2:3]1.[C:12](O[C:17](=[O:20])[CH2:18][CH3:19])(=O)[CH2:13][CH3:14].[C:21]([OH:26])(=[O:25])[C:22]([OH:24])=[O:23]>C(O)C>[C:21]([O-:26])(=[O:25])[C:22]([O-:24])=[O:23].[CH3:1][NH+:2]1[CH2:7][CH2:6][C:5]([C:8]2[N:9]=[C:12]([CH2:13][CH3:14])[O:11][N:10]=2)=[CH:4][CH2:3]1.[CH3:1][NH+:2]1[CH2:7][CH2:6][C:5]([C:8]2[N:10]=[C:17]([CH2:18][CH3:19])[O:20][N:9]=2)=[CH:4][CH2:3]1

Participants

5

Reactant 3

HCID 971Oxalic AcidHCID 31263Propionic anhydrideHCID 85553776HCID 85553776, compound

Product 1

HCID 23047488HCID 23047488, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of 1-methyl-1,2,5,6-tetrahydropyridin-4-carboxamide oxime (200 mg; 1.0 mmol) in propionic anhydride (5 ml; 39 mmol) was stirred at 80° C. for 20 hours. After evaporation in vacuo, the residue was dissolved in aqueous sodium hydroxide (4N) (5 ml) and extracted with ether (4×25 ml). The combined ether phases were dried (MgSO4), filtered, and evaporated in vacuo. To a solution of the residue in ethanol (5 ml) a solution of oxalic acid (90 mg; 1.0 mmol) in ethanol (5 ml) was added. Crystallization with ether gave the title compound. M.P. 190°-191° C.

Workup

  1. customAfter evaporation in vacuo
  2. dissolutionthe residue was dissolved in aqueous sodium hydroxide (4N) (5 ml)
  3. extractionextracted with ether (4×25 ml)
  4. dry with materialThe combined ether phases were dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customCrystallization with ether

Sources & evidence

ORD record
ord-3265db69abb646f5b115af8dd0c811e1
Source dataset
uspto-grants-1990_06
Patent number
US04933353

Reaction notes

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