4-Aminobenzonitrile → 4-(1H-Pyrrol-1-yl)benzonitrile

HRID 224692Notes

Reaction equation

HRID 224692 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.CO[CH:12]1[CH2:16][CH2:15][CH:14](OC)O1>C1(C)C=CC=CC=1>[N:1]1([C:2]2[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=2)[CH:12]=[CH:16][CH:15]=[CH:14]1

Participants

4

Reactant 2

HCID 133964-AminobenzonitrileHCID 790982,5-Dimethoxytetrahydrofuran

Product 1

HCID 2724244-(1H-Pyrrol-1-yl)benzonitrileYield 60.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 4-aminobenzonitrile (50 g., 0.42 mole), 2,5-dimethoxytetrahydrofuran (56 g., 0.42 mole) and 4 A molecular sieves (184 g) in toluene (560 ml) was heated under reflux for 24 hrs. The residue from evaporation was washed with pet. ether and then recrystallized from diisopropyl ether to yield 42.5 g (60%) of 4-(1-pyrrolyl)-benzonitrile, m.p. 104°-106° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 24 hrs
  3. customThe residue from evaporation
  4. washwas washed with pet. ether
  5. customrecrystallized from diisopropyl ether

Sources & evidence

ORD record
ord-1a534788f15d4878a0a31cebd1c8a754
Source dataset
uspto-grants-1980_11
Patent number
US04233452

Reaction notes

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