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

HRID 1445300Notes

Reaction equation

HRID 1445300 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-f016881d3e9f48bf9d138243e62a3dd7
Source dataset
uspto-grants-2010_02
Patent number
US07666647B2

Reaction notes

Loading…