4-Aminobenzonitrile → 4-(1H-Pyrrol-1-yl)benzonitrile
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]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
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
- temperaturewas heated
- temperatureunder reflux for 24 hrs
- customThe residue from evaporation
- washwas washed with pet. ether
- 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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