3-Cyano-7-hydroxy-4-methylcoumarin → HCID 136387768, Verbindung

HRID 579438Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 579438
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([CH3:15])=[C:7]([C:13]#[N:14])[C:8](=[O:12])[O:9]2)=[CH:4][CH:3]=1.[NH4+]=[S:17]>CN(C)C=O>[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([CH3:15])=[C:7]([C:13](=[S:17])[NH2:14])[C:8](=[O:12])[O:9]2)=[CH:4][CH:3]=1

Komponenten

3

Edukt 1

HCID 53931723-Cyano-7-hydroxy-4-methylcoumarin

Produkt 1

HCID 136387768HCID 136387768, VerbindungAusbeute 36,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 7-Hydroxy-4-methyl-2-oxo-2H-chromene-3-carbonitrile (7.50 g, 37.31 mmol) in N,N-dimethylformamide (150 mL), ammonium sulfide (40-48 wt. % solution in water; 38 mL, 560 mmol) was added, and the resulted mixture was stirred at room temperature for a week. An additional portion of ammonium sulfide (38 mL) was added on every second day. The solution was evaporated and the solid residue was triturated with water, filtered and dried. The obtained crude product was purified by column chromatography (Kieselgel 60), with chloroform-methanol (1:1) as eluent. The title compound (3.20 g, 13.6 mmol, 36%) was isolated as a yellow powder,

Aufarbeitung

  1. customThe solution was evaporated
  2. customthe solid residue was triturated with water
  3. filtrationfiltered
  4. customdried
  5. customThe obtained crude product
  6. customwas purified by column chromatography (Kieselgel 60), with chloroform-methanol (1:1) as eluent

Quellen und Nachweise

ORD-Eintrag
ord-30b67dfb2de145eeaae157fb6a32826c
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09040714B2

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