Ammonia → 3-(4-Acetyl-phenylamino)-4-amino-cyclobut-3-ene-1,2-dione

HRID 10724

Reaction equation

HRID 10724 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1.C([O:15][C:16]1[C:17](=O)[C:18](=O)[C:19]=1[O:20]CCCC)CCC.[NH3:27]>C(O)C>[C:8]([C:5]1[CH:6]=[CH:7][C:2]([NH:1][C:18]2[C:19](=[O:20])[C:16](=[O:15])[C:17]=2[NH2:27])=[CH:3][CH:4]=1)(=[O:10])[CH3:9]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 7468p-AminoacetophenoneHCID 65108Dibutyl squarate

Product 1

HCID 219810423-(4-Acetyl-phenylamino)-4-amino-cyclobut-3-ene-1,2-dioneYield 52.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ex-102A: To a solution of 2.7 g (20 mmol) of 4′-aminoacetophenone in 90 mL of ethanol, 4.5 g (20 mmol) of 3,4-dibutoxy-3-cyclobutene-1,2-dione (Aldrich) was added. The mixture was then heated to reflux overnight. A light yellow precipitate formed. To the reaction mixture, 20 mL (40 mmol) of ammonia (2.0 M in ethanol) was added, and the resultant mixture was stirred at room temperature for 2 hr. The light yellow solid was filtered and washed with ethanol to give 2.4 g (52%) of 3-(4-acetyl-phenylamino)-4-amino-cyclobut-3-ene-1,2-dione. 1H-NMR (DMSO-d6) δ 9.99 (br, 1H), 7.90 (d, J=8 Hz, 2H), 7.50 (d, J=8 Hz, 2H), 4.31 (br, 2H), 2.48 (s, 3H). HMRS (EI) calcd. for C12H10N2O3: 230.0691; found: 230.0691.

Workup

  1. temperatureThe mixture was then heated
  2. temperatureto reflux overnight
  3. customA light yellow precipitate formed
  4. filtrationThe light yellow solid was filtered
  5. washwashed with ethanol

Sources & evidence

ORD record
ord-607dcb3ea567495abab93b0af0ab0fe9
Source dataset
uspto-grants-2006_08
Patent number
US07094801B2

Linked notes

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