Hydrochloric Acid → (Z)-6-hydroxy-2-[(5-nitro-1H-indol-3-yl)methylene]benzofuran-3(2H)-one

HRID 1749730Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1749730
[OH:1][C:2]1[CH:11]=[CH:10][C:5]2[C:6](=[O:9])[CH2:7][O:8][C:4]=2[CH:3]=1.[N+:12]([C:15]1[CH:16]=[C:17]2[C:21](=[CH:22][CH:23]=1)[NH:20][CH:19]=[C:18]2[CH:24]=O)([O-:14])=[O:13].Cl>C(O)C>[OH:1][C:2]1[CH:11]=[CH:10][C:5]2[C:6](=[O:9])/[C:7](=[CH:24]/[C:18]3[C:17]4[C:21](=[CH:22][CH:23]=[C:15]([N+:12]([O-:14])=[O:13])[CH:16]=4)[NH:20][CH:19]=3)/[O:8][C:4]=2[CH:3]=1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 2357176-Hydroxy-3-coumaranoneHCID 2460395-nitro-1H-indole-3-carbaldehyde

Produkt 1

HCID 71278726(Z)-6-hydroxy-2-[(5-nitro-1H-indol-3-yl)methylene]benzofuran-3(2H)-oneAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A solution of 6-hydroxybenzofuran-3(2H)-one (0.400 g, 2.7 mmol) and 5-nitro-1H-indole-3-carboxaldehyde (0.56 g, 2.9 mmol) in ethanol (5.0 mL) was added with concentrated hydrochloric acid (1.0 mL), and the mixture was stirred at 70° C. for 3 hours. The reaction mixture was cooled to room temperature, and then the solid was collected by filtration, and washed with methanol to obtain (Z)-6-hydroxy-2-[(5-nitro-1H-indol-3-yl)methylene]benzofuran-3(2H)-one (0.77 g, 90%).

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationthe solid was collected by filtration
  3. washwashed with methanol

Quellen und Nachweise

ORD-Eintrag
ord-b2c8dc259b0445cdaa3f7d4d335e0ba9
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09156827B2

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