Réaction #1598

ord-64d1801cfcd4465887e5bc7221651fa5

Équation de réaction

O=C(O)CCCC(=O)c1ccccc1
4-benzoylbutyric acid
NN
hydrazine
O
water
O=c1cccc(-c2ccccc2)nn1
desired product
Rendement 39.0%
O=c1cccc(-c2ccccc2)nn1
7-phenyl-1,2-diazapin-3-one
Rendement 39.0%

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    workup.ADDITIONwas added in one portion
  2. 2
    Températurethe reaction was heated
  3. 3
    TempératureThe reaction mixture was cooled
  4. 4
    Lavagewashed with H2O (100 ml) and brine (100 ml)
  5. 5
    ExtractionThe ether extract
  6. 6
    Séchagewas dried over anhydrous MgSO4
  7. 7
    Filtrationfiltered
  8. 8
    Autreto yield an orange semisolid which
  9. 9
    Autrewas triturated with ether

Mode opératoire

To a mixture of 10 g (0.052 mole) of 4-benzoylbutyric acid in 300 ml of toluene, hydrazine was added in one portion and the reaction was heated to reflux until all water had ceased to azeotrope. The reaction mixture was cooled and the toluene was stripped off in vacuo. The residue was dissolved in 200 ml Et2O and washed with H2O (100 ml) and brine (100 ml). The ether extract was dried over anhydrous MgSO4, filtered and stripped to yield an orange semisolid which was triturated with ether to yield 3.8 g (39%) of the desired product as a yellow solid.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US05726162uspto-grants-1998_03