Oxalic Acid → HCID 23047517, compound

HRID 1904299Notes

Reaction equation

HRID 1904299 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]=[C:4]([C:8](=[N:10][OH:11])[NH2:9])[CH2:3]1.[C:12]([OH:17])(=[O:16])[C:13]([OH:15])=[O:14].[CH3:18][CH2:19][O:20][CH2:21][CH3:22]>C(OC(=O)C)(=O)C.C(O)C>[C:12]([O-:17])(=[O:16])[C:13]([O-:15])=[O:14].[CH3:1][NH+:2]1[CH2:7][CH2:6][CH:5]=[C:4]([C:8]2[N:9]=[C:18]([CH3:19])[O:11][N:10]=2)[CH2:3]1.[CH3:1][NH+:2]1[CH2:7][CH2:6][CH:5]=[C:4]([C:8]2[N:10]=[C:21]([CH3:22])[O:20][N:9]=2)[CH2:3]1

Participants

6

Reactant 3

HCID 971Oxalic AcidHCID 3283Diethyl EtherHCID 85553771HCID 85553771, compound

Product 1

HCID 23047517HCID 23047517, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 7918Acetic AnhydrideSolvent

Procedure

A solution of 1-methyl-1,2,5,6-tetrahydropyridin-3-carboxamide oxime (200 mg; 1.29 mmol) in acetic anhydride (5 ml) was heated at 80° C. for 24 hours. After evaporation in vacuo the residue was dissolved in 4N NaOH (5 ml) and extracted with ether (3×25 ml). The ether phases were dried (MgSO4), filtered, and evaporated in vacuo. The residue was dissolved in ethanol (99.9%)(5 ml) and added to a solution of oxalic acid (100 mg; 1.1 mmol) in ethanol (99.9%)(5 ml). Addition of ether gave the title compound in a yield of 52%. M.P. 173°-174° C.

Workup

  1. customAfter evaporation in vacuo the residue
  2. dissolutionwas dissolved in 4N NaOH (5 ml)
  3. extractionextracted with ether (3×25 ml)
  4. dry with materialThe ether phases were dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. dissolutionThe residue was dissolved in ethanol (99.9%)(5 ml)

Sources & evidence

ORD record
ord-89200aa5ac714961858733c71b266384
Source dataset
uspto-grants-1989_06
Patent number
US04837241

Reaction notes

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