Hydrazine → 6-Ethyl-3,5-dimethoxy-pyridine-2-carboxylic acid hydrazide

HRID 76098Notes

Reaction equation

HRID 76098 reaction equation
C([O:3][C:4]([C:6]1[C:11]([O:12][CH3:13])=[CH:10][C:9]([O:14][CH3:15])=[C:8]([CH2:16][CH3:17])[N:7]=1)=O)C.[NH2:18][NH2:19]>O1CCOCC1>[CH2:16]([C:8]1[N:7]=[C:6]([C:4]([NH:18][NH2:19])=[O:3])[C:11]([O:12][CH3:13])=[CH:10][C:9]=1[O:14][CH3:15])[CH3:17]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 669865986-Ethyl-3,5-dimethoxy-pyridine-2-carboxylic acid ethyl ester

Product 1

HCID 669866196-Ethyl-3,5-dimethoxy-pyridine-2-carboxylic acid hydrazideYield 71.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A flask was charged with 6-ethyl-3,5-dimethoxy-pyridine-2-carboxylic acid ethyl ester (50 mg.; 0.21 mmol), dioxane (4 mL) and hydrazine (64 mg; 2 mmol). The reaction was heated at reflux for one hour, and all solvents were removed by evaporation. To the dried cake was added ethyl acetate (10 mL) and a 10% aqueous sodium carbonate solution (1 mL). The organic layer was isolated, dried with magnesium sulfate, and evaporated to give 6-ethyl-3,5-dimethoxy-pyridine-2-carboxylic acid hydrazide (34 mg.; 0.15 mmol).

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for one hour
  3. customall solvents were removed by evaporation
  4. additionTo the dried cake was added ethyl acetate (10 mL)
  5. customThe organic layer was isolated
  6. dry with materialdried with magnesium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-0a3cd662d34d493eaf23971aabb78c58
Source dataset
uspto-grants-2014_09
Patent number
US08835464B2

Reaction notes

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