2-Amino-5-nitrobenzonitrile → 5-nitro-2-(1H-pyrrol-1-yl)benzonitrile

HRID 2290547Notes

Reaction equation

HRID 2290547 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:3]=1[C:4]#[N:5].CO[CH:15]1[CH2:19][CH2:18][CH:17](OC)O1>C(O)(=O)C>[N+:10]([C:7]1[CH:8]=[CH:9][C:2]([N:1]2[CH:15]=[CH:19][CH:18]=[CH:17]2)=[C:3]([CH:6]=1)[C:4]#[N:5])([O-:12])=[O:11]

Participants

4

Reactant 2

HCID 285322-Amino-5-nitrobenzonitrileHCID 790982,5-Dimethoxytetrahydrofuran

Product 1

HCID 27742935-nitro-2-(1H-pyrrol-1-yl)benzonitrileYield 106.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

In a manner similar to Example 1, Step A, the reaction of 30.0 g (0.18 mole) of 2-amino-5-nitrobenzonitrile with 28.7 g (0.22 mole) of 2,5-dimethoxytetrahydrofuran in 60 ml of glacial acetic acid produced 41.0 g of 5-nitro-2-(1H-pyrrol-1-yl)benzonitrile.

Sources & evidence

ORD record
ord-59b2c55a24af43c5beec4929e8d87b11
Source dataset
uspto-grants-1986_10
Patent number
US04617316

Reaction notes

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