N-(5-Amino-2-hydroxy-2-(4-isopropyl-2-methoxyphenyl)-1,3-dioxo-2,3-dihydro-1H-inden-4-yl)acetamide → 4,5-Diamino-2-hydroxy-2-(4-isopropyl-2-methoxyphenyl)-2H-inden-1,3-dione

HRID 527135Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 527135
[NH2:1][C:2]1[C:3]([NH:25]C(=O)C)=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[C:6]([OH:23])([C:12]1[CH:17]=[CH:16][C:15]([CH:18]([CH3:20])[CH3:19])=[CH:14][C:13]=1[O:21][CH3:22])[C:5]2=[O:24]>Cl.CO.C(Cl)Cl>[NH2:25][C:3]1[C:2]([NH2:1])=[CH:10][CH:9]=[C:8]2[C:4]=1[C:5](=[O:24])[C:6]([OH:23])([C:12]1[CH:17]=[CH:16][C:15]([CH:18]([CH3:20])[CH3:19])=[CH:14][C:13]=1[O:21][CH3:22])[C:7]2=[O:11]

Komponenten

5

Edukt 1

HCID 71477133N-(5-Amino-2-hydroxy-2-(4-isopropyl-2-methoxyphenyl)-1,3-dioxo-2,3-dihydro-1H-inden-4-yl)acetamide

Produkt 1

HCID 714771354,5-Diamino-2-hydroxy-2-(4-isopropyl-2-methoxyphenyl)-2H-inden-1,3-dioneAusbeute 46,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 313Hydrochloric AcidLösungsmittelHCID 887MethanolLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

N-(5-amino-2-hydroxy-2-(4-isopropyl-2-methoxyphenyl)-1,3-dioxo-2,3-dihydro-1H-inden-4-yl)acetamide (85 mg, 0.19 mmol) was completely dissolved in 6M HCl (1.4 ml) and methanol (0.1 ml), followed by heating for 40 min at 80. The reaction mixture was diluted with methylene chloride, extracted with 2N NaOH aqueous solution, and the concentrated organic layer was purified using column chromatography (ethylacetate:hexane=1:1) to afford the title compound (30 mg, 44%).

Aufarbeitung

  1. temperatureby heating for 40 min at 80
  2. extractionextracted with 2N NaOH aqueous solution
  3. customthe concentrated organic layer was purified

Quellen und Nachweise

ORD-Eintrag
ord-bb13e9f2e9ff411395a63a5e984908fa
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09346749B2

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