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

HRID 357288Notes

Reaction equation

HRID 357288 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[NH2:10])[C:5]#[N:6].[CH3:11][CH2:12][O:13][C:14]1[C:18](=O)[C:16](=[O:17])[C:15]=1[O:20]CC.CCCCCC.C(OCC)(=O)C>C(O)C>[CH2:12]([O:13][C:14]1[C:15](=[O:20])[C:16](=[O:17])[C:18]=1[NH:10][C:9]1[CH:8]=[CH:7][C:4]([C:5]#[N:6])=[CH:3][C:2]=1[OH:1])[CH3:11]

Participants

6

Reactant 4

HCID 8058HexaneHCID 8857Ethyl AcetateHCID 123228Diethyl squarateHCID 101977194-Amino-3-hydroxybenzonitrile

Product 1

HCID 105153373-Ethoxy-4-(2-hydroxy-4-cyanoanilino)-3-cyclobutene-1,2-dione

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3-hydroxy-4-aminobenzonitrile (1.08 g, 0.008 mol) and diethyl squarate (1.19 ml, 0.008 mol) in dry ethanol (22 ml) was heated at 85° C. for two days. During the course of the reaction, a tan precipitate forms. TLC (1:1 hexane:ethyl acetate) indicates that no starting material is present. The solid is filtered through a Buchner funnel, washed with cold ethanol, and collected to give 3-ethoxy-4-(2-hydroxy-4-cyanophenyl)amino-3-cyclobutene-1,2-dione, 1.19 g (0.0046 mol, 57%).

Workup

  1. customDuring the course of the reaction
  2. filtrationThe solid is filtered through a Buchner funnel
  3. washwashed with cold ethanol
  4. customcollected

Sources & evidence

ORD record
ord-10d913221c944cdabe4ab967f0bd31e2
Source dataset
uspto-grants-1998_11
Patent number
US05840764

Reaction notes

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