Phenylhydrazine → HCID 12632313, compound

HRID 1683809Notes

Reaction equation

HRID 1683809 reaction equation
[CH3:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([C:8](C)(C)[C:9]([O:11]CC)=O)=O)=[CH:4][CH:3]=1.[C:18]1([NH:24][NH2:25])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[C:18]1([N:24]2[C:9](=[O:11])[CH2:8][C:6]([C:5]3[CH:4]=[CH:3][C:2]([CH3:1])=[CH:17][CH:16]=3)=[N:25]2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 7516PhenylhydrazineHCID 521998p-Toluenesulfonic acid monohydrateHCID 19041234HCID 19041234, compound

Product 1

HCID 12632313HCID 12632313, compoundYield 93.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 15 g (64 mmol) of ethyl α-(4-methylbenzoyl)isobutyrate, 10 g (93 mmol) of phenyl-hydrazine and 100 ml of toluene was dehydrated under reflux in the presence of p-toluenesulfonic acid monohydrate (catalytic amount) for 18 hours. The reaction solution was washed successively with 1N sodium hydroxide, 1N hydrochloric acid and saturated brine solution, and dried over anhydrous magnesium sulfate. Then the solvent was evaporated under reduced pressure. The obtained crude product was recrystallized from methanol to give 15 g of the object compound as white crystals (yield 84%).

Workup

  1. washThe reaction solution was washed successively with 1N sodium hydroxide, 1N hydrochloric acid and saturated brine solution
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customThen the solvent was evaporated under reduced pressure
  4. customThe obtained crude product
  5. customwas recrystallized from methanol

Sources & evidence

ORD record
ord-2e9cadc04c5d49d1bbb9e19eb637f841
Source dataset
uspto-grants-1997_06
Patent number
US05639776

Reaction notes

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