Methylhydrazine → 2-Methylphthalazin-1-one

HRID 839498Notes

Reaction equation

HRID 839498 reaction equation
BrC[CH:3](CBr)[C:4]1[C:5]([C:10]([OH:12])=O)=[CH:6][CH:7]=[CH:8][CH:9]=1.[CH3:15][NH:16][NH2:17]>C(O)C>[CH3:15][N:16]1[N:17]=[CH:3][C:4]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:10]1=[O:12]

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 70621097alpha,alpha-Dibromomethyl-o-toluic acid

Product 1

HCID 3133782-Methylphthalazin-1-oneYield 75%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 29.4 g (0.1 mole) of α,α-dibromomethyl-o-toluic acid and 14.7 g (0.32 mole) of methylhydrazine in 100 ml of ethanol was heated under reflux for 3 hours. The solvent was evaporated under reduced pressure, and the residue recrystalized from ethanol to give 12.0 g (yield: 75%) of 2-methyl-1-phthalazinone having a melting point of 111°-112° C.

Workup

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

Sources & evidence

ORD record
ord-79b5af5e5e9a42f79021de6d70749cab
Source dataset
uspto-grants-1978_06
Patent number
US04096143

Reaction notes

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