Ethanol → 1-[2-(Aminooxy)-2-methylpropionyl]-2-[(1,4-dihydro-5-hydroxy-4-oxo-2-pyridyl)carbonyl]hydrazine

HRID 345174Notes

Reaction equation

HRID 345174 reaction equation
[OH:1][C:2]1[C:3](=[O:29])[CH:4]=[C:5]([C:8]([NH:10][NH:11][C:12](=[O:28])[C:13]([CH3:27])([O:15][N:16]2C(=O)C3=CC=CC=C3C2=O)[CH3:14])=[O:9])[NH:6][CH:7]=1.CNN.C(O)C>CN(C)C=O>[NH2:16][O:15][C:13]([CH3:27])([CH3:14])[C:12]([NH:11][NH:10][C:8]([C:5]1[NH:6][CH:7]=[C:2]([OH:1])[C:3](=[O:29])[CH:4]=1)=[O:9])=[O:28]

Participants

5

Reactant 3

HCID 702EthanolHCID 6061MethylhydrazineHCID 199939011-[(1,4-Dihydro-5-hydroxy-4-oxo-2-pyridyl)carbonyl]-2-[2-methyl-2-(phthalimidooxy)propionyl]hydrazine

Product 1

HCID 199939031-[2-(Aminooxy)-2-methylpropionyl]-2-[(1,4-dihydro-5-hydroxy-4-oxo-2-pyridyl)carbonyl]hydrazine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.670 g (1.675 mmol) of 1-[(1,4-dihydro-5-hydroxy-4-oxo-2-pyridyl)carbonyl]-2-[2-methyl-2-(phthalimidooxy)propionyl]hydrazine was dissolved in 1.5 ml of dimethylformamide and treated with 0.077 g (1.675 mmol) of methylhydrazine. After stirring for 21/2 hours at room temperature about 2 ml of ethanol were added. The crystals obtained were filtered off and discarded. The filtrate was evaporated under strongly reduced pressure and the product was crystallized from ethanol. 1-[2-(aminooxy)-2-methylpropionyl]-2-[(1,4-dihydro-5-hydroxy-4-oxo-2-pyridyl)carbonyl]hydrazine was obtained as white crystals melting at 234° (dec.).

Workup

  1. additionwere added
  2. customThe crystals obtained
  3. filtrationwere filtered off
  4. customThe filtrate was evaporated under strongly reduced pressure
  5. customthe product was crystallized from ethanol

Sources & evidence

ORD record
ord-8b4477e3c4604d1095e21ef7e87ecab3
Source dataset
uspto-grants-1991_10
Patent number
US05055572

Reaction notes

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