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

HRID 1706407Notes

Reaction equation

HRID 1706407 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 4A 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-fcc08d14595a44be8de04a162ee93a80
Source dataset
uspto-grants-1980_06
Patent number
US04207329

Reaction notes

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