Diethyl squarate → 3-Ethoxy-4-(2-hydroxy-4-cyanoanilino)-3-cyclobutene-1,2-dione

HRID 1743149Notes

Reaction equation

HRID 1743149 reaction equation
C(O[C:4]1[C:5](=[O:12])[C:6](=[O:11])[C:7]=1[O:8][CH2:9][CH3:10])C.[OH:13][C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][C:21]=1[NH2:22])[C:17]#[N:18]>C(O)C>[CH2:9]([O:8][C:7]1[C:6](=[O:11])[C:5](=[O:12])[C:4]=1[NH:22][C:21]1[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[CH:15][C:14]=1[OH:13])[CH3:10]

Participants

4

Reactant 2

HCID 123228Diethyl squarateHCID 101977194-Amino-3-hydroxybenzonitrile

Product 1

HCID 105153373-Ethoxy-4-(2-hydroxy-4-cyanoanilino)-3-cyclobutene-1,2-dioneYield 53.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3,4-diethoxy-3-cyclobutene-1,2-dione (1.2 mL, 8.12 mmol) and 3-hydroxy-4-aminobenzonitrile (1.25 g, 8.11 mmol) in ethanol was heated at 85° C. for overnight. A tan precipitates forms. The solid was filtered, and collected. 1.12 g (53%) of 3-ethoxy-4-(2-hydroxy-4-cyanoanilino)-3-cyclobutene-1,2-dione was obtained. LC/MS(H+) 259

Workup

  1. customA tan precipitates forms
  2. filtrationThe solid was filtered
  3. customcollected

Sources & evidence

ORD record
ord-43f187c7d38f490fb40c6e015b4bef71
Source dataset
uspto-grants-2006_03
Patent number
US07008962B2

Reaction notes

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