Hydrazine, dihydrochloride → Ethyl 6-[4-(benzyloxy)phenyl]-3-oxo-2,3-dihydropyridazine-4-carboxylate

HRID 970187Notes

Reaction equation

HRID 970187 reaction equation
Cl.Cl.[NH2:3][NH2:4].O[C:6]([CH2:17][C:18]([C:20]1[CH:25]=[CH:24][C:23]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[CH:22][CH:21]=1)=O)([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:7](OCC)=[O:8]>C(O)C>[CH2:27]([O:26][C:23]1[CH:24]=[CH:25][C:20]([C:18]2[CH:17]=[C:6]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:7](=[O:8])[NH:3][N:4]=2)=[CH:21][CH:22]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

4

Reactant 2

HCID 17548Hydrazine, dihydrochlorideHCID 59018085HCID 59018085, compound

Product 1

HCID 59018088Ethyl 6-[4-(benzyloxy)phenyl]-3-oxo-2,3-dihydropyridazine-4-carboxylateYield 78.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.69 g of hydrazine dihydrochloride were added, at a temperature in the region of 19° C., to 5.6 g of diethyl hydroxy[2-(4-benzyloxyphenyl)-2-oxoethyl]malonate dissolved in 180 cm3 of ethanol. The reaction medium was heated and maintained at reflux for 12 hours. After cooling, the solvent was removed under reduced pressure (2 kPa; 55° C.). The solid residue was triturated in 20 cm3 of ethanol, suction-filtered through a sinter funnel and oven-dried under reduced pressure (10 kPa; 50° C.). 3.85 g of ethyl 6-[4-(benzyloxy)phenyl]-3-oxo-2,3-dihydropyridazine-4-carboxylate were obtained in the form of a green solid melting at 239° C.

Workup

  1. temperatureThe reaction medium was heated
  2. temperaturemaintained
  3. temperatureat reflux for 12 hours
  4. temperatureAfter cooling
  5. customthe solvent was removed under reduced pressure (2 kPa; 55° C.)
  6. customThe solid residue was triturated in 20 cm3 of ethanol
  7. filtrationsuction-filtered through a sinter funnel
  8. customoven-dried under reduced pressure (10 kPa; 50° C.)

Sources & evidence

ORD record
ord-a2bca365aaf24ee4a13c97e1b81d1364
Source dataset
uspto-grants-2007_12
Patent number
US07309701B2

Reaction notes

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