Aniline → 1-Phenyl-2,5-dihydro-1H-pyrrole

HRID 366869

Reaction equation

HRID 366869 reaction equation
[CH3:1]/[CH:2]=[CH:3]\[CH3:4].[NH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>C1(C)C=CC=CC=1>[C:6]1([N:5]2[CH2:4][CH:3]=[CH:2][CH2:1]2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 6115AnilineHCID 5287573cis-2-BUTENE

Product 1

HCID 50604391-Phenyl-2,5-dihydro-1H-pyrroleYield 90%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 60.0 g of the cis-2-butene derivative solution prepared in Example 1 and 250 g of toluene in a round flask reactor, 149.0 g (1.6 mol) of aniline was added dropwise with stirring for 30 min. at 50° C. After 2 hours of stirring, the crystallized solid was removed by filtration; 42.0 g of 35% HCl (aq) was added to the filtrate, and then excess benzylamine hydrochloride was removed by filtration or extraction. After the solvent was evaporated under reduced pressure, 52.2 g of 1-phenyl-3-pyrroline (yield 90.0%) was obtained.

Workup

  1. stirringAfter 2 hours of stirring
  2. customthe crystallized solid was removed by filtration
  3. addition42.0 g of 35% HCl (aq) was added to the filtrate
  4. customexcess benzylamine hydrochloride was removed by filtration or extraction
  5. customAfter the solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-b17f0fae9d664117a622fa1b257a71d3
Source dataset
uspto-grants-2000_10
Patent number
US06130338

Linked notes

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