Cyanoacetic acid hydrazide → 3-Oxo-5-phenyl-2,3-dihydro-pyridazine-4-carbonitrile

HRID 133016

Reaction equation

HRID 133016 reaction equation
[C:1]1([C:7]([CH:9]=O)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:11]([CH2:13][C:14]([NH:16][NH2:17])=[O:15])#[N:12]>C(O)C>[O:15]=[C:14]1[C:13]([C:11]#[N:12])=[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:9]=[N:17][NH:16]1

Participants

4

Reactant 2

HCID 8820Cyanoacetic acid hydrazideHCID 14090Phenylglyoxal

Product 1

HCID 597350963-Oxo-5-phenyl-2,3-dihydro-pyridazine-4-carbonitrile

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Phenyl glyoxal (1.0 g, 7.46 mmol) and cyanoacetohydrazide (740 mg, 7.46 mmol) were heated to reflux in 10 mL ethanol for 16 hours. After cooling, the solvent was evaporated and the crude brown mixture was purified by silica chromatography (1:9 methanol/dichloromethane). The still impure product was further recrystallized from methanol affording 70 mg pure product.

Workup

  1. temperatureAfter cooling
  2. customthe solvent was evaporated
  3. customthe crude brown mixture was purified by silica chromatography (1:9 methanol/dichloromethane)
  4. customThe still impure product was further recrystallized from methanol affording 70 mg pure product

Sources & evidence

ORD record
ord-5f81c07103d8477b9ab602dbda118848
Source dataset
uspto-grants-2008_06
Patent number
US07390808B2

Linked notes

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