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

HRID 1927324Notes

Reaction equation

HRID 1927324 reaction equation
[C-:1]#[N:2].[Na+].[NH2:4][C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][CH:6]=1.[C:12]1(=O)[CH2:15][CH2:14][CH2:13]1.C(OCC)(=O)C>C(O)(=O)C>[CH3:11][C:8]1[CH:9]=[CH:10][C:5]([NH:4][C:12]2([C:1]#[N:2])[CH2:15][CH2:14][CH2:13]2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 7813p-ToluidineHCID 8857Ethyl AcetateHCID 8929Sodium CyanideHCID 14496Cyclobutanone

Product 1

HCID 609877761-(4-Methylphenyl)aminocyclobutanenitrileYield 92%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Sodium cyanide (0.147 g, 3 mmol) was added to a mixture of p-toluidine (0.214 g, 2 mmol) and cyclobutanone (0.21 g, 3 mmol) in 90% acetic acid (3 ml). The reaction mixture was stirred at room temperature for 12 h and then 20 ml of ethyl acetate was added. The organic layer was washed with water (3×10 ml), dried over magnesium sulfate and concentrated under vacuum to dryness to yield 1-(4-methylphenyl)aminocyclobutanenitrile, 7a (0.343 g, 1.84 mmol, 92%) as a brown solid.

Workup

  1. washThe organic layer was washed with water (3×10 ml)
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated under vacuum to dryness

Sources & evidence

ORD record
ord-8131dcb1d1b14431b0b77237eb14fd39
Source dataset
uspto-grants-2012_05
Patent number
US08183274B2

Reaction notes

Loading…