Hydrochloric Acid → N-(7-Amino-2-hydroxy-2-(4-isopropyl-2-methoxyphenyl)-1,3-dioxo-2,3-dihydro-1H-inden-4-yl)acetamide

HRID 527132Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 527132
[OH:1][C:2]1([C:20]2[CH:25]=[CH:24][C:23]([CH:26]([CH3:28])[CH3:27])=[CH:22][C:21]=2[O:29][CH3:30])[C:10](=[O:11])[C:9]2[C:4](=[C:5]([N+:16]([O-])=O)[CH:6]=[CH:7][C:8]=2[NH:12][C:13](=[O:15])[CH3:14])[C:3]1=[O:19].Cl.O>C(O)C.[Fe]>[NH2:16][C:5]1[CH:6]=[CH:7][C:8]([NH:12][C:13](=[O:15])[CH3:14])=[C:9]2[C:4]=1[C:3](=[O:19])[C:2]([OH:1])([C:20]1[CH:25]=[CH:24][C:23]([CH:26]([CH3:27])[CH3:28])=[CH:22][C:21]=1[O:29][CH3:30])[C:10]2=[O:11]

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 71476974N-(2-hydroxy-2-(4-isopropyl-2-methoxyphenyl)-7-nitro-1,3-dioxo-2,3-dihydro-1H-inden-4-yl)acetamide

Produkt 1

HCID 71477132N-(7-Amino-2-hydroxy-2-(4-isopropyl-2-methoxyphenyl)-1,3-dioxo-2,3-dihydro-1H-inden-4-yl)acetamideAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

N-(2-hydroxy-2-(4-isopropyl-2-methoxyphenyl)-7-nitro-1,3-dioxo-2,3-dihydro-1H-inden-4-yl)acetamide (0.10 g, 0.24 mmol) was completely dissolved in anhydrous ethanol (3 ml). This solution was added with iron (0.098 g), conc. HCl (0.05 ml) and water (0.3 ml). The reaction mixture was heated for 2 hrs under reflux. After filtration at high temperature to remove iron, the filtrate was concentrated in a vacuum and purified using column chromatography (ethylacetate:hexane=1:2) to afford the title compound (65 mg, 71%).

Aufarbeitung

  1. temperatureThe reaction mixture was heated for 2 hrs
  2. temperatureunder reflux
  3. filtrationAfter filtration at high temperature
  4. customto remove iron
  5. concentrationthe filtrate was concentrated in a vacuum
  6. custompurified

Quellen und Nachweise

ORD-Eintrag
ord-d5a55c45de464977b7452fcc307801d6
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09346749B2

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