Diethyl squarate → 3-Ethoxy-4-(2-hydroxy-6-cyanophenyl)amino-3-cyclobutene-1,2-dione

HRID 357293

Reaktionsgleichung

Reaktionsgleichung von HRID 357293
[NH2:1][C:2]1[C:9]([OH:10])=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[CH3:11][CH2:12][O:13][C:14]1[C:18](=O)[C:16](=[O:17])[C:15]=1[O:20]CC>C(O)C>[CH2:12]([O:13][C:14]1[C:15](=[O:20])[C:16](=[O:17])[C:18]=1[NH:1][C:2]1[C:3]([C:4]#[N:5])=[CH:6][CH:7]=[CH:8][C:9]=1[OH:10])[CH3:11]

Komponenten

4

Edukt 2

HCID 123228Diethyl squarateHCID 159063362-Amino-3-hydroxybenzonitrile

Produkt 1

HCID 111187243-Ethoxy-4-(2-hydroxy-6-cyanophenyl)amino-3-cyclobutene-1,2-dione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of 2-amino-3-hydroxybenzonitrile (1.00 g, 0.0075 mol) and diethyl squarate (1.10 ml, 0.0075 mol) in dry ethanol (20 ml) was heated at 85° C. for three days. During the course of the reaction, a tan precipitate forms. The solid is filtered through a Buchner funnel, washed with cold ethanol, adsorbed on silica gel, and flash chromatographed using hexane/ethyl acetate (2:1) as the eluant to give 3-ethoxy-4-(2-hydroxy-6-cyanophenyl)amino-3-cyclobutene-1,2-dione, 0.50 g (0.0019 mol, 26%).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-2aacc83dbd0643d9a2c620b27b88fcb9
Quelldatensatz
uspto-grants-1998_11
Patentnummer
US05840764

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