Hydrazine hydrate (1:1) → 6-Chloro-1,2-dihydrophthalazin-1-one

HRID 839497Notes

Reaction equation

HRID 839497 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[C:4]([CH:11](Cl)Cl)[CH:3]=1.O.[NH2:15][NH2:16]>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:9][CH:10]=1)[C:6](=[O:7])[NH:16][N:15]=[CH:11]2

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 11085870Benzoic acid, 4-chloro-2-(dichloromethyl)-

Product 1

HCID 122985416-Chloro-1,2-dihydrophthalazin-1-oneYield 63.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 23.9 g (0.1 mole) of 4-chloro-2-dichloromethylbenzoic acid and 16 g (0.32 mole) of hydrazine hydrate in 200 ml of ethanol was heated under reflux for 3 hours. The ethanol was evaporated under reduced pressure, and the residue recrystallized from ethanol to give 11.4 g (yield: 63%) of 6-chloro-1-phthalazinone having a melting point of 272°-273° C.

Workup

  1. temperatureunder reflux for 3 hours
  2. customThe ethanol was evaporated under reduced pressure
  3. customthe residue recrystallized from ethanol

Sources & evidence

ORD record
ord-a4c966434adc403e888707450cf3aa29
Source dataset
uspto-grants-1978_06
Patent number
US04096143

Reaction notes

Loading…