Aniline → 4-Phenylamino-3-penten-2-one 97

HRID 556385Notes

Reaction equation

HRID 556385 reaction equation
[CH3:1][C:2](=O)[CH2:3][C:4](=[O:6])[CH3:5].[NH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[C:9]1([NH:8]/[C:2](/[CH3:1])=[CH:3]\[C:4](=[O:6])[CH3:5])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 6115AnilineHCID 31261AcetylacetoneHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 57053294-Phenylamino-3-penten-2-one 97

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 2,4-pentanedione (51.5 mL), aniline (45.6 mL) and a catalytic amount of para-toluenesulfonic acid monohydrate (0.95 g) in toluene (500 ml) was refluxed for 3.5 h in a round bottom flask equipped with a Dean-Stark apparatus and condenser. The solution was concentrated to dryness to give the desired compound as an orange oil (89.3 g).

Workup

  1. customequipped with a Dean-Stark apparatus and condenser
  2. concentrationThe solution was concentrated to dryness

Sources & evidence

ORD record
ord-86a721848f4d4b6a9b34b0e1f8da085f
Source dataset
uspto-grants-2011_11
Patent number
US08058263B2

Reaction notes

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