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

HRID 1879595Notes

Reaction equation

HRID 1879595 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-eed78bf7abb640ed84db0717a84e533a
Source dataset
uspto-grants-2012_11
Patent number
US08318467B2

Reaction notes

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