Phenylhydrazine → HCID 3778426, compound

HRID 1683814Notes

Reaction equation

HRID 1683814 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]([C:9](C)(C)[C:10]([O:12]CC)=O)=O)[CH:2]=1.[C:17]1([NH:23][NH2:24])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH2:9][C:10](=[O:12])[N:23]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[N:24]=2)[CH:2]=1

Participants

5

Reactant 3

HCID 7516PhenylhydrazineHCID 521998p-Toluenesulfonic acid monohydrateHCID 19041236HCID 19041236, compound

Product 1

HCID 3778426HCID 3778426, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 1.5 g (6.8 mmol) of ethyl α-(3-pyridylcarbonyl)isobutyrate and 0.88 g (12 mmol) of phenyl hydrazine was dissolved in 50 ml of toluene, and the solution was dehydrated and heated under reflux in the presence of p-toluenesulfonic acid monohydrate (catalytic amount) for 18 hours. The reaction solution was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=3/2 (v/v)) to give 1.5 g of the object compound as white crystals (yield 83%).

Workup

  1. temperatureheated
  2. concentrationThe reaction solution was concentrated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=3/2 (v/v))

Sources & evidence

ORD record
ord-526f0f308ba44dc7b4ea19f0051a3e75
Source dataset
uspto-grants-1997_06
Patent number
US05639776

Reaction notes

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