Acetic Acid → HCID 178498788, compound

HRID 399798Notes

Reaction equation

HRID 399798 reaction equation
C[N:2](C)[CH:3]=[CH:4][C:5]([C:7]1[CH:8]=[C:9]([C:13]([O:15][CH3:16])=[O:14])[CH:10]=[N:11][CH:12]=1)=O.C(O)(=O)C.O.[NH2:23]N>CO>[NH:2]1[CH:3]=[CH:4][C:5]([C:7]2[CH:8]=[C:9]([C:13]([O:15][CH3:16])=[O:14])[CH:10]=[N:11][CH:12]=2)=[N:23]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 24654Hydrazine hydrate (1:1)HCID 53719482Methyl 5-(3-dimethylamino-1-oxo-2-propenyl)-3-pyridinecarboxylate

Product 1

HCID 178498788HCID 178498788, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The mixture of methyl 5-(3-dimethylamino-1-oxo-2-propenyl)-3-pyridinecarboxylate (1.7 g), acetic acid (0.62 ml) and hydrazine monohydrate (0.53 ml) in methanol (34 ml) was stirred for 24 hours at ambient temperature, and the mixture was evaporated in vacuo. To the residue was added a mixture of tetrahydrofuran, ethyl acetate and water, and the mixture was adjusted to pH 9 with potassium carbonate. The separated organic layer was washed with brine and dried over magnesium sulfate. The solvent was removed by concentration and the residue was triturated with diisopropyl ether to give methyl 5-(pyrazol-3-yl)-3-pyridinecarboxylate (1.24 g).

Workup

  1. customthe mixture was evaporated in vacuo
  2. additionTo the residue was added
  3. additiona mixture of tetrahydrofuran, ethyl acetate and water
  4. washThe separated organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was removed by concentration
  7. customthe residue was triturated with diisopropyl ether

Sources & evidence

ORD record
ord-60fa09f41b834aff9d0a00a53e53aef1
Source dataset
uspto-grants-1998_10
Patent number
US05824691

Reaction notes

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