p-Toluidine → 1-(4-Methylphenyl)aminocyclobutanenitrile

HRID 244976Notes

Reaction equation

HRID 244976 reaction equation
C[Si]([C:5]#[N:6])(C)C.[NH2:7][C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=1.[C:15]1(=O)[CH2:18][CH2:17][CH2:16]1>ClCCl>[CH3:14][C:11]1[CH:12]=[CH:13][C:8]([NH:7][C:15]2([C:5]#[N:6])[CH2:18][CH2:17][CH2:16]2)=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 7813p-ToluidineHCID 14496CyclobutanoneHCID 82115Trimethylsilyl cyanide

Product 1

HCID 609877761-(4-Methylphenyl)aminocyclobutanenitrileYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trimethylsilyl cyanide (0.93 ml, 7 mmol) was added dropwise to a mixture of p-toluidine (0.535 g, 5 mmol) and cyclobutanone (0.42 g, 6 mmol). The reaction mixture was stirred at room temperature for 6 h and then concentrated under vacuum to obtain a brown liquid which was subjected to chromatography (dichloromethane) to yield 1-(4-methylphenyl)aminocyclobutanenitrile, 7a (0.912 g, 4.9 mmol, 98%) as a yellowish solid.

Workup

  1. concentrationconcentrated under vacuum
  2. customto obtain a brown liquid which

Sources & evidence

ORD record
ord-c63782e3e06140a096d94b5185f90c73
Source dataset
uspto-grants-2014_02
Patent number
US08658681B2

Reaction notes

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