3-Aminobenzonitrile → HCID 10610174, compound

HRID 1733898Notes

Reaction equation

HRID 1733898 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[C:5]#[N:6].[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:3]=[C:4]([CH:7]=[CH:8][CH:9]=2)[C:5]#[N:6])=[C:13]1[O:12][CH2:10][CH3:11]

Participants

4

Reactant 2

HCID 167023-AminobenzonitrileHCID 123228Diethyl squarate

Product 1

HCID 10610174HCID 10610174, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-Aminobenzonitrile (2.06 g, 17.4 mmol) was added to a solution of 3,4-diethoxy-3-cyclobutene-1,2-dione (2.97 g, 17.5 mmol) in absolute ethanol (50 mL). The mixture was heated at reflux overnight. The mixture was cooled and the resulting yellow precipitate was collected by vacuum filtration. Yield: 3.40 g (81%): 1H NMR (DMSO-d6): δ 10.95 (s, 1H), 7.75-7.40 (m, 4H), 4.73 (q, 2H), 1.39 (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-110932a61e674e4b8f25b29870512ed8
Source dataset
uspto-grants-1996_07
Patent number
US05532245

Reaction notes

Loading…