Hydrazine → HCID 67314713, compound

HRID 240386Notes

Reaction equation

HRID 240386 reaction equation
[C:1]([CH:9]([C:15](=O)[CH3:16])[C:10]([O:12][CH2:13][CH3:14])=[O:11])(=O)[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.[NH2:18][NH2:19].C(=O)([O-])O.[Na+]>C(O)C>[CH3:16][C:15]1[NH:19][N:18]=[C:1]([C:2]2[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=2)[C:9]=1[C:10]([O:12][CH2:13][CH3:14])=[O:11]

Participants

5

Reactant 3

HCID 9321HydrazineHCID 516892Sodium BicarbonateHCID 67314215Ethyl 2-isonicotinoyl-3-oxobutanoate

Product 1

HCID 67314713HCID 67314713, compoundYield 81.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl 2-isonicotinoyl-3-oxobutanoate (8.0 g) in ethanol (80 mL) was added hydrazine (1.7 g), and the mixture was stirred at room temperature for 1 hr, and poured into saturated aqueous sodium hydrogen carbonate solution. The mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (6.4 g).

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-1fae0dbfe206417fbcce5495037785e0
Source dataset
uspto-grants-2014_02
Patent number
US08648079B2

Reaction notes

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