4-Aminobenzonitrile → 4-[(2-Ethoxy-3,4-dioxocyclobut-1-en-1-yl)amino]benzonitrile

HRID 1733896Notes

Reaction equation

HRID 1733896 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[CH2:10]([O:12][C:13]1[C:14](=O)[C:15](=[O:20])[C:16]=1[O:17]CC)[CH3:11]>C(O)C>[O:17]=[C:16]1[C:15](=[O:20])[C:14]([NH:1][C:2]2[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=2)=[C:13]1[O:12][CH2:10][CH3:11]

Participants

4

Reactant 2

HCID 133964-AminobenzonitrileHCID 123228Diethyl squarate

Product 1

HCID 108240584-[(2-Ethoxy-3,4-dioxocyclobut-1-en-1-yl)amino]benzonitrile

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-Aminobenzonitrile (3.47 g, 29.4 mmol) was added to a solution of 3,4-diethyoxy-3-cyclobutene-1,2-dione (5.00 g, 29.4 mmol) in absolute ethanol (100 mL). The mixture was heated at reflux overnight. The mixture was cooled, and the resulting yellow precipitate was collected by vacuum filtration. Yield: 2.60 g (37%): mp 218°-222° C.; 1H NMR (DMSO-d6): δ11.07 (s, 1H), 7.81 (d, 2H), 7.56 (d, 2H), 4.79 (q, 2H), 1.46 (t, 3H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux overnight
  3. temperatureThe mixture was cooled
  4. filtrationthe resulting yellow precipitate was collected by vacuum filtration

Sources & evidence

ORD record
ord-a1f784c5eaa0457192bdb2df56887f7d
Source dataset
uspto-grants-1996_07
Patent number
US05532245

Reaction notes

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