Water → 7-Phenyl-1,2-diazapin-3-one

HRID 2115

Reaction equation

HRID 2115 reaction equation
[C:1]([CH2:9][CH2:10][CH2:11][C:12]([OH:14])=O)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[NH2:16][NH2:17]>C1(C)C=CC=CC=1.CCOCC>[C:2]1([C:1]2[N:17]=[N:16][C:12](=[O:14])[CH:11]=[CH:10][CH:9]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 962WaterHCID 9321HydrazineHCID 73914delta-Oxobenzenepentanoic acid

Product 1

HCID 856459747-Phenyl-1,2-diazapin-3-oneYield 39%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

To a mixture of 10g (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.

Workup

  1. additionwas added in one portion
  2. temperaturethe reaction was heated
  3. temperatureThe reaction mixture was cooled
  4. washwashed with H2O (100 ml) and brine (100 ml)
  5. extractionThe ether extract
  6. dry with materialwas dried over anhydrous MgSO4
  7. filtrationfiltered
  8. customto yield an orange semisolid which
  9. customwas triturated with ether

Sources & evidence

ORD record
ord-eff35b6820384eb2a5f2f60a585c840d
Source dataset
uspto-grants-1998_03
Patent number
US05728698

Linked notes

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