Toluene → 4-isopropylbenzohydrazide

HRID 1622611Notes

Reaction equation

HRID 1622611 reaction equation
[CH3:1][CH:2]([C:4]1[CH:13]=[CH:12][C:7]([C:8](OC)=[O:9])=[CH:6][CH:5]=1)[CH3:3].O.[NH2:15][NH2:16].C1(C)C=CC=CC=1.C(=O)([O-])O.[Na+]>CO>[CH3:1][CH:2]([C:4]1[CH:13]=[CH:12][C:7]([C:8]([NH:15][NH2:16])=[O:9])=[CH:6][CH:5]=1)[CH3:3]

Participants

6

Reactant 4

HCID 1140TolueneHCID 24654Hydrazine hydrate (1:1)HCID 227855Methyl cumateHCID 516892Sodium Bicarbonate

Product 1

HCID 2194004-isopropylbenzohydrazideYield 92.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of methyl 4-(1-methylethyl)benzoate (10 g) and hydrazine monohydrate (5.62 g) in methanol (50 mL) was heated under reflux overnight. To the reaction mixture was added toluene (50 ml), and the mixture was heated at 120° C. overnight. The reaction mixture was added to a saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was washed with hexane and diisopropyl ether to give the title compound (9.22 g) as a white solid.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux overnight
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. washThe residue was washed with hexane and diisopropyl ether

Sources & evidence

ORD record
ord-eb88e2a1f780401195edbedd197747db
Source dataset
uspto-grants-2014_07
Patent number
US08778934B2

Reaction notes

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